Reaction #1182

Reaction equation

SnCl2

NaNO2

5-amino-2-chlorobenzoic acid

→

expected product

Yield 123.1%

5-Hydrazino-2-chlorobenzoic acid hydrochloride

Yield 123.1%

Solvents

HCl

water

water

HCl

Conditions

Workup

1. 1
   Temperaturecooled to -10° C.
2. 2
   workup.STIRRINGThe mixture is stirred for one and a half hours at 0° C.
3. 3
   Filtrationfiltered
4. 4
   Otherthe precipitate is dried

Procedure

A solution of 2.11 g of NaNO2 in 40 ml of water is added over 30 minutes to a suspension, cooled to -2° C., of 5 g of 5-amino-2-chlorobenzoic acid in 50 ml of concentrated HCl. The solution is stirred for 2 hours at -3° C. and cooled to -10° C., and a solution of 23 g of SnCl2 ·2H2O in 20 ml of concentrated HCl and 20 ml of water is added over 30 minutes. The mixture is stirred for one and a half hours at 0° C. and filtered, and the precipitate is dried to obtain 4 g of expected product.

Source