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CAS No. : | 1588-83-6 | MDL No. : | MFCD00017009 |
Formula : | C7H6N2O4 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | ZZNAYFWAXZJITH-UHFFFAOYSA-N |
M.W : | 182.13 | Pubchem ID : | 74115 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-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 |
---|---|---|
89.7% | Example 1 Preparation of 4-iodo-3-nitrobenzoic acid (Compound V) 45 g (0.25 mol) 4-Amino-3-nitrobenzoic acid, 400 ml water and 100 ml concentrated hydrochloric acid were added into a reaction flask. Started to stir, and the mixture was cooled to 0 to 5 C., then 50 ml aqueous solution of 25.9 g sodium nitrite (0.38 mol) was added dropwise. The solid was dissolved gradually. After completing the dropwise addition, the mixture was reacted at 0 to 5 C. for 1 hour, and 200 ml aqueous solution of 88 g (0.5 mol) potassium iodide was added dropwise at this temperature. The mixture was stirred at room temperature for 2 h after completing the dropwise addition, and solid was precipitated. The solid was filtered, washed with water, and dried to obtain 4-iodo-3-nitrobenzoic acid (compound V) as a solid, 65 g (0.22 mol), yield 89.7%. | |
Preparation of {l-Methanesulfonyl-6- [5- (2-phenoxy-ethylsulfanylmethyl)- [1,3, 4] oxadiazol-2-yl]-1 H-indol-2-ylmethyl}-dimethyl-amine a) 4-Iodo-3-nitro-benzoic acid An acetone solution of 4-amino-3-nitrobenzoic acid (25 g, 137.26 mmol, 1 eq. ) was cooled in an ice bath and treated with an aqueous solution of sodium nitrite (10.42 g, 150.99 mmol, 1.1 eq. ) and the reaction stirred for 30 minutes. The reaction was then treated with an aqueous solution of potassium iodide (23.01 g, 138.63 mmol, 1.01 eq. ) and the reaction warmed to 40C. After 2 hours, the acetone was removed in vacuo and the reaction extracted 2X250 mL with ethyl acetate. The organics were washed with 5M aqueous HCl and then collected, dried, filtered, and the solvent removed in vacuo. The residue was purified by normal phase chromatography using a step gradient of ethyl acetate in hexanes as the mobile phase to give 4-iodo-3-nitro-benzoic acid as an orange solid. This material was taken on to the esterification reaction as is. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 15: Preparation of 3-cyano-5-nitro-benzoic acid; Solution 1: 3-Amino-5-nitro-benzoic acid (10 g, 54.9 mmol) was dissolved in aqueous hydrochloric acid (concentrated) (55 ml) and diluted with water (200 ml). A solution of sodium nitrite (3.788 g, 54.90 mmol) in water (30 ml) was added at 0-5 0C.Solution 2: To a solution of copper sulfate hydrate (28.786 g, 115.29 mmol) in water (120 ml) was added a solution of potassium cyanide (27.528g, 422.73 mmol) in water (30 ml).Solution 2 was heated to 65C. The pH of Solution 1 was adjusted to 6-7 with aqueous sodium carbonate (saturated) at 0-5C. Solution 1 was added dropwise to Solution 2 at 65C. The reaction mixture was heated to reflux for 40 minutes. The reaction mixture was allowed to cool to ambient temperature and acidified with aqueous hydrochloric acid (2N). The aqueous phase was extracted three times with ethyl acetate (3x 200 ml). The combined organic extracts were washed with aqueous sodium phosphite (saturated), water, brine and concentrated to give 3-cyano-5-nitro-benzoic acid (7.2 g, 68 % yield) which was used without further purification. 1H-NMR (400 MHz, DMSOd6): 9.0 (s, IH), 8.82 (s, IH), 8.70 (s, IH) ppm. |