2-Amino-5-iodo-3-methylbenzoic Acid → 2-Amino-5-cyano-3-methylbenzoic acid

Temperature

150 °C

A mixture of 1.0 g of 2-amino-5-iodo-3-methylbenzoic acid, 0.45 g of copper cyanide and 10 ml of N,N-dimethylformamide was stirred at 150° C. for 9 hours. The reaction mixture was concentrated under reduced pressure. Into the residue, 20 ml of water and 2 ml of ethylenediamine were poured, and the mixture was stirred at room temperature for 1 hour. After the reaction mixture was filtered, the filtrate was adjusted to around pH 5 by an addition of concentrated hydrochloric acid, and then extracted with ethyl acetate three times. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure to obtain 0.40 g of 2-amino-5-cyano-3-methylbenzoic acid of the formula:

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additionInto the residue, 20 ml of water and 2 ml of ethylenediamine were poured
3. stirringthe mixture was stirred at room temperature for 1 hour
4. filtrationAfter the reaction mixture was filtered
5. additionthe filtrate was adjusted to around pH 5 by an addition of concentrated hydrochloric acid
6. extractionextracted with ethyl acetate three times
7. dry with materialThe combined organic layer was dried over sodium sulfate
8. concentrationconcentrated under reduced pressure

ORD record

ord-c006a1f5e57347bfbc3b005969a7a53b

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07867949B2