Reaction #1180

Reaction equation

SnCl2

NaNO2

4-amino-3-methoxybenzoic acid

→

4-Hydrazino-3-methoxybenzoic acid hydrochloride

Solvents

HCl

water

H2O

HCl

Conditions

Workup

1. 1
   Temperaturethe mixture is cooled to -10° C.
2. 2
   workup.STIRRINGAfter one and a half hours of stirring at -10° C.
3. 3
   Filtrationthe mixture is filtered
4. 4
   Washthe precipitate is washed with 50 ml of pentane
5. 5
   Otherto obtain
6. 6
   Otherafter drying

Procedure

A solution of 2.17 g of NaNO2 in 40 ml of H2O is added slowly to a solution, cooled to 0° C., of 5 g of 4-amino-3-methoxybenzoic acid in 50 ml of concentrated HCl. After 1 hour 15 minutes of stirring at 0° C., the mixture is cooled to -10° C., and a solution of 23.6 g of SnCl2 ·2H2O in 20 ml of concentrated HCl and 20 ml of water is added over 30 min. After one and a half hours of stirring at -10° C., the mixture is filtered, and the precipitate is washed with 50 ml of pentane to obtain, after drying, 6 g of expected product.

Source