Reaction #1178

Reaction equation

NaNO2

SnCl2

4-amino-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid

→

hydrazine

Yield 73.3%

4-Hydrazino-5,6,7,8-tetrahydro-1-naphthalene-carboxylic acid hydrochloride

Yield 73.3%

Solvents

water

HCl

HCl

Conditions

Workup

1. 1
   workup.STIRRINGThe mixture is stirred for 1 hour at RT
2. 2
   Filtrationfiltered
3. 3
   Washthe product is washed with concentrated HCl
4. 4
   Otherdried under a stream of dry nitrogen

Procedure

A solution of 0.26 g of NaNO2 in 1 ml of water is added to a solution, cooled to -5° C., of 0.73 g of 4-amino-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid in 10 ml of concentrated HCl. After one and a half hours of stirring at -5° C., a solution of 3.4 g of SnCl2 ·2H2O in 34 ml of concentrated HCl is added at -5° C. The mixture is stirred for 1 hour at RT and filtered, and the product is washed with concentrated HCl and dried under a stream of dry nitrogen to obtain 0.67 g of the expected hydrazine.

Source