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Jang, Mingyeong ; Lim, Taeho ; Park, Byoung Yong , et al. JOC,2022,87(2):910-919. DOI: 10.1021/acs.joc.1c01431 PubMed ID: 34983185
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Abstract: In this study, we developed a metal-free and highly chemoselective method for the reduction of aromatic nitro compounds. This reduction was performed using tetrahydroxydiboron [B2(OH)4] as the reductant and 4,4'-bipyridine as the organocatalyst and could be completed within 5 min at room temperature. Under optimal conditions, nitroarenes with sensitive functional groups, such as vinyl, ethynyl, carbonyl, and halogen, were converted into the corresponding anilines with excellent selectivity while avoiding the undesirable reduction of the sensitive functional groups.
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CAS No. : | 3544-24-9 | MDL No. : | MFCD00007989 |
Formula : | C7H8N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GSCPDZHWVNUUFI-UHFFFAOYSA-N |
M.W : | 136.15 | Pubchem ID : | 1645 |
Synonyms : |
3-Aminobenzamide; 3-ABA
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21.52% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; | <Example 26> 3-[2-(4-bromo-phenoxy)aceryl-amino]-benzamide <n="36"/>To a mixture of (4-bromo-phenoxy)-acetic acid (392.5 mg, 1.8 mmol), 3-amino-benzamide (408.2 mg,3.0 mmol), N<3-dimethylaminopropyl)-N'-etiiyl carbodiimideHCl (EDC) (517.6 mg, 2.7 mmol) and 1- hydroxybenzotriazole (HOBt) (365.3 mg, 2.7 mmol) in DMF (18 mL) was added N, N-dsopropylefhyamine, redistilled (DIPEA) (0.47 ml, 2.7 mmol). The mixture was stirred overnight, and then partitioned between ethyl acetate and water. The organic phase was washed with brine, dried (MgSO4 anh), and concentrated. The residue was purified by recrystallization fi"om the mixture of Ethyl acetate and MeOH to give 3-[2-(4-bromo- phenoxy)acetyl-amino]-benzamide as a white solid (134.9 mg, 21.52% yield).1HNMR (DMSO-dg) 10.21 (IH, s, NH), 8.09 (IH, s, aromatic-H), 7.94 (IH, s, MH2), 7.79 (IH, d, J =8.1 Hz5 aromatic-H), 7.35 - 7.59 (5H, m, aromatic-H, NH2), 6.99 (2H, d, J = 9.3 Hz, aromatic-H), 4.72 (2H, s, CH2). |
21.52% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; | To a mixture of (4-bromo-phenoxyacetic acid (392.5 mg, 1.8 mmol), 3-amino-benzamide (408.2 mg, 3.0 mmol), N-(3-ethylaminopropyl)-N'-ethyl carbodiimide HCl (EDC) (517.6 mg, 2.7 mmol) and 1-hydroxybenzotriazole (HOBt) (365.3 mg, 2.7 mmol) in DMF (18 mL) was added N,N-diisopropylethylamine, redistilled (DIPEA) (0.47 ml, 2.7 mmol). The mixture was stirred overnight and then partitioned between ethyl acetate and water. The organic phase was washed with brine, dried (MgSO4 anh), and concentrated. The residue was purified by recrystallization from the mixture of Ethyl acetate and MeOH to give 3-[2-(4-bromo-phenoxy)acetyl-amino]-benzamide as a white solid (134.9 mg, 21.52% yield). 1H-NMR (DMSO-d6) 10.21 (1H, s, NH), 8.09 (1H, s, aromatic-H), 7.94 (1H, s, NH2), 7.79 (1H, d, J=8.1 Hz, aromatic-H), 7.35-7.59 (5H, m, aromatic-H, NH2), 6.99 (2H, d, J=9.3 Hz aromatic-H), 4.72 (2H, s, CH2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; | EXAMPLE 2: Preparation of 3- (3-lNo.-indol-3-yl-acryloylamino) - benzamide; In 5.0 mL of dimethylformamide were dissolved 3-(1H- indol-3-yl) -acrylic acid (187 mg, 1.0 mmol) and 3-amino- benzamide (68.1 mg, 0.5 mmol), followed by the addition of benzotriazol-1-yl-oxitripyrrolidino phosphonium hexafluorophosphate (520.3 g, 1.0 mmol) and N, N- diisopropylethyl amine (0.17 ml, 1.0 mmol). The resulting solution was stirred at room temperature and mixed with ethyl acetate and an aqueous sodium salt solution. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and purified using silica gel column chromatography (/i-hexane : ethyl acetate : methanol = 5:3:1) to produce the subject <n="25"/>compound (2) as a yellow solid (34.3 mg, 23%).1H-NMR (CD3OD, 300Hz): 8.17 (IH, s, Aromatic), 7.83-7.97 (3H, m, Aromatic), 7.58 (2H, m, Aromatic), 7.41 (2H, m, Aromatic), 7.19 (2H, m, Aromatic), 6.77 (IH, d, J = 15.9 Hz, Aromatic) . |
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; | 1-2. Method for synthesis of low-molecular-weight compound RSC-133 (8b) [0135] Among the above-described low-molecular-weight compounds, RSC-133 (3-[3-(1H-indol-3-yl)-acrylamido]-benzamide (8b)) was synthesized in the following manner. [0136] First, trans-3-indoleacrylic acid (7a) and 3-amino-benzamide (6b) were dissolved in DMF, and benzotriazol-1-yl-N-oxy-tris(pyrrolidino)-phosphonium hexafluorophosphate (PyBOP) and N,N-diisopropylethylamine (DIPEA) were added to the solution to perform a coupling reaction. The reaction solution was stirred overnight at room temperature. The resulting material was separated and purified to obtain 3-[3-(1H-indol-3-yl)-acrylamido]-benzamido (RSC-133) as a yellow solid. The chemical characteristics and purity of RSC-133 were analyzed by 1H NMR (FIG. 6) and HPLC (FIG. 7). 1H NMR (CDCl3, 300 MHz) d = 8.90 (s, 1H), 8.21 (s, 1H), 7.86-8.03 (m, 4H), 7.76 (d, J = 8.1 Hz, 1H), 7.36-7.41 (m, 3H), 7.20 (m, 2H), 6.60 (d, J = 15.3 Hz, 2H), 3.88 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With pyridine; In dichloromethane; N,N-dimethyl-formamide; at 0℃; for 1.16667h; | To a stirring solution of 3-aminobenzamide (6.0 g, 44.1 mmol), DCM (100 mL), DMF (30 inL) and pyridine (35 g, 36 mL, 441 mmol), at 0 C (ice-bath), was added 2-fluoro-5- (trifluoromethyl)benzoyl chloride (10 g, 44.1 mmol) dropwise over a period of 10 minutes. The reaction mixture was stirred at 0 C for 1 hour, the ice bath was removed, and the reaction mixture was allowed to stir at room temperature for 4 hours. The reaction mixture was filtered and the solid was washed with a minimum amount of ethyl acetate and water. The obtained solid was dried in a vacuum oven to yield N- (3-carbamoylphenyl)-2-fluoro-5-(trifluoromethyl)benzamide (12.7 g, 88%) as an off-white solid. ESI-MS m/z calc. 326.08, found 327.3 (M+l)+; retention time (Method B): 1.39 (3 minute run). NMR (400 MHz, DMSO-d6) δ 10.73 (s, 1H), 8.20 - 8.14 (m, 1H), 8.08 (dd, J = 6.1, 2.4 Hz, 1H), 8.06 - 7.93 (m, 2H), 7.87 (dd, J = 7.9, 2.1 Hz, 1H), 7.69 - 7.59 (m, 2H), 7.45 (t, J = 7.9 Hz, 1H), 7.40 (s, 1H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With acetic acid; at 110℃; for 4h; | General procedure: The starting materials 1 and 2 were commercially available (Energy Chemical, Shanghai, China).Compound 2 (3.72 mmol) was added to a stirred solution of compound 1 (3.38 mmol) in glacial aceticacid (10 mL). The reaction mixture was then stirred at 110 C for 4 h. After completion of the reaction,the solvent was evaporated, and the residue was purified on a silica gel column chromatography andeluted with ethyl acetate/petroleum ether (bp 60-90 C) (1:3, v/v) to give compounds 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With pyridine; dmap; at 20℃; for 1.5h;Inert atmosphere; | Step 1: A round bottom flask was charged with 3-aminobenzamide (500 mg, 3.67 mmol) and 4-dimethylaminopyridine (22.4 mg, 0.05 eq) and flushed with nitrogen. Anhydrous pyridine (7.34 mL) was added followed by 3-fluoro-5-(trifluoromethyl)benzoyl chloride (837 μL, 5.50 mmol), and the reaction mixture was stirred at ambient temperature for 1.5 hours. Water (20 mL) was added, and the reaction mixture was stirred for 10 minutes. The mixture was filtered through a fritted funnel, and the precipitate was rinsed with water and a small amount of acetonitrile, then air dried to afford N-(3-carbamoylphenyl)-3-fluoro- 5-(trifluoromethyl)benzamide (726 mg, 2.22 mmol, 61.0 %) as a white powder |
61% | With pyridine; dmap; at 20℃; for 1.5h;Inert atmosphere; | Step 1: A round bottom flask was charged with 3-aminobenzamide (500 mg, 3.67 mmol) and 4-dimethylaminopyridine (22.4 mg, 0.05 eq) and flushed with nitrogen. Anhydrous pyridine (7.34 mL) was added followed by 3-fluoro-5-(trifluoromethyl)benzoyl chloride (837 μL, 5.50 mmol), and the reaction mixture was stirred at ambient temperature for 1.5 hours. Water (20 mL) was added, and the reaction mixture was stirred for 10 minutes. The mixture was filtered through a fritted funnel, and the precipitate was rinsed with water and a small amount of acetonitrile, then air dried to afford N-(3-carbamoylphenyl)-3-fluoro- 5-(trifluoromethyl)benzamide (726 mg, 2.22 mmol, 61.0 %) as a white powder |