Stannous Chloride → 3-Hydrazino-4-methylbenzoic acid hydrochloride

Participants

Reaction Steps

To a suspension of 3-amino-4-methylbenzoic acid (5.0 g, 33 mmol) in concentrated HCl (31 mL) cooled to below −5 ° C. was added a solution of NaNO2 (2.4 g, 35 mmol) in water (12 mL) at such rate that the temperature remained below −4 ° C. After stirring for 45 min, the suspension was transferred to a cold stirred solution of SnCl2 (28 g, 124 mmol) in concentrated HCl (18 mL) via pipette. The resulting solid was collected via vacuum filtration and washed first with cold water and then with Et2O. The solid was recrystallized from water/2-propanol (10:1) to provide 3-hydrazino-4-methyl-benzoic acid hydrochloride. (2.23 g, 33%) as a pink solid. ESI MS m/z 167 [C8H10N2O2+H]+.

Provenance & Evidence