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CAS No. : | 2305-36-4 | MDL No. : | MFCD00047853 |
Formula : | C8H9NO2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | RPGKFFKUTVJVPY-UHFFFAOYSA-N |
M.W : | 151.16 | Pubchem ID : | 75316 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | |
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 |
---|---|---|
69% | Compound 22 (3.00 g, 19.8 mmol) in dry DMF (100 mL) under Ar was treated with EDC.HCl (4.17 g, 21.8 mmol) and HOBt (3.33 g, 21.8 mmol) for 3 h, after which aq. NH3 (35%, 20 mL) was added and the mixture was stirred for 16 h. The evaporation residue, in EtOAc, was washed twice with water and with brine. Drying and evaporation gave 25 (2.04 g, 69%) as an off-white solid: mp 151-153 C (lit. [62] mp 148 C); 1H NMR ((CD3)2SO) delta 2.22 (3 H, s, Me), 6.35 (1 H, dd, J = 8.0, 1.2, 5-H), 6.52 (1 H, d, J = 0.5 Hz, 3-H), 6.57 (2 H, s, NH2), 6.95 (1 H, brs, CONHH), 7.48 (1 H, d, J = 8.0 Hz, 6-H), 7.65 (1 H, brs, CONHH); 13C NMR ((CD3)2SO) (HSQC/HMBC) delta 21.03 (Me), 111.14 (1-C), 115.61 (5-C), 116.44 (3-C), 128.77 (6-C), 141.55 (2-C), 150.31 (4-C), 171.19 (C=O). | |
64% | With N-hydroxybenzotriazole ammonium salt; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20℃; for 1h; | To a stirred solution of 2-amino-4-methyl-benzoic acid (300 mg, 1.99 mmol) in THF (6 mL),EDC.HCl (569 mg, 2.98 mmol), HOBt·NH3 (447 mg, 2.98 mmol) and DIPEA (1.06 mL, 5.96mmol) were added at RT and stirred for 1 h (TLC indicated complete consumption of startingmaterial). The reaction mixture was diluted with water (30 mL), extracted with EtOAc (3 x25 mL). The combined organic extracts were dried over Na2S04, concentrated under reducedpressure to give the crude compound which was purified by flash column chromatography(100-200 silica gel, 5 g, 50% EtOAc-Hexane) to afford 2-amino-4-methyl-benzamide (190mg, 64%) as a white solid 1H NMR [300 MHz, DMSO-d6]: J 7.62 (brs, 1H), 7.42 (d, J = 8.1 Hz, 1H), 6.93 (brs, 1H),6.54-6.46 (m, 3H), 6.30- 6.27 (m, 1H), 2.15 (s, 3H). |
60% | With ammonia; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In methanol; N,N-dimethyl-formamide; at 20℃; for 24h;Inert atmosphere; | Accordingtoaliteratureprocedure,3toasolutionof2-amino-3-methylbenzoicacid(151mg,1.00mmol,1.0eq)indegassedDMF(2.00mL)wereaddedHOBt(162mg,1.20mmol,1.2eq.),EDCI.HCl(230mg,1.20mmol,1.2eq.),N,N-diisopropylethylamine(350muL,2.00mmol,2.0eq),and7MNH3/MeOH(429muL,1.50mmol,1.5eq.).Thesolutionwasstirredatroomtemperaturefor24hoursthenpouredoverwaterandtheaqueouslayerextractedwithEtOAc(320mL),thecombinedorganiclayerswashedwithbrine(25mL),driedwithNa2SO4andconcentratedinvacuo.TheresiduewaspurifiedbyFCC(gradient50%EtOAc/hexanes to 80% EtOAc/hexanes) to give 2-amino-3-methylbenzamide (90.0 mg,0.599mmol,60%)asawhiteamorphoussolid;mp:144-146C,lit.144-145C. |
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