Reaction #1183

Reaction equation

NaNO2

SnCl2

3-amino-4-methylbenzoic acid

→

3-Hydrazino-4-methylbenzoic acid hydrochloride

Solvents

water

HCl

HCl

AcOH

Conditions

Workup

1. 1
   workup.WAITthe mixture is left
2. 2
   TemperatureAfter cooling to -10° C.
3. 3
   workup.STIRRINGAfter stirring for 1 hour at RT
4. 4
   Filtrationfiltration
5. 5
   Washwashing of the precipitate with 5 ml of 1N HCl
6. 6
   Dryingdrying over P2O5 under vacuum, 6.15 g of the expected product
7. 7
   Otherare obtained

Procedure

A solution of 2.74 g of NaNO2 in 28 ml of water is added over 30 minutes to a solution, cooled to -5° C., of 5 g of 3-amino-4-methylbenzoic acid in 120 ml of concentrated HCl and 40 ml AcOH, and the mixture is left stirring for 1 hour 20 minutes at 0° C. After cooling to -10° C., a solution of 27.6 g of SnCl2 ·2H2O in 28 ml of concentrated HCl is added slowly. After stirring for 1 hour at RT, filtration, washing of the precipitate with 5 ml of 1N HCl and drying over P2O5 under vacuum, 6.15 g of the expected product are obtained.

Source