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ChemicalBook CAS DataBase List 5-Nitroanthranilonitrile
17420-30-3

5-Nitroanthranilonitrile synthesis

11synthesis methods
A newer synthetic route starts from 6-nitroisatoic anhydride [2H-3,1-benzoxazine-6-nitro-2,4 (1H)-dione]: the latter is converted into 2-amino-5-nitrobenzonitrile by reaction with ammonia, subsequent treatment with phosgene in dimethylformamide or Nmethylpyrrolidone, followed by hydrolysis of the formamidine.
2-Amino-5-nitrobenzonitril synthesis
-

Yield:17420-30-3 72%

Reaction Conditions:

with sodium carbonate in N,N-dimethyl-formamide at 140; for 1 h;

Steps:

3.1 2-amino-5-nitrobenzonitrile (20)
A mixture of compound 12 (4.18g, 0.02mol) and Na2CO3 (1.0g) in DMF (40ml) was heated to 140°C for 1h. The mixture was poured into 100ml of ice water. The solution was extracted with CH2Cl2 (50ml×3). The organic phase was washed three times with water and then dried over anhydrous sodium sulfate and evaporated under reduce pressure, giving crude product as brown liquid. The curde product was purified by column chromatography over silica gel (using petroleum / EtOAc=2:1) to afford 20 as a yellow solid 2.34g with a yield of 72%. mp 208~210°C.

References:

Wang, Zheng;Wu, Xue;Wang, Li;Zhang, Jiao;Liu, Jianli;Song, Zhongxing;Tang, Zhishu [Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,# 11,p. 2589 - 2593] Location in patent:supporting information

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