Reaction #4479

Reaction equation

tin

hydrochloric acid

3-methoxyaniline

hydrochloric acid

sodium nitrite

→

title compound

(3-methoxyphenyl)hydrazine hydrochloride

Solvents

water

Conditions

Workup

1. 1
   Otherat ca. 0°
2. 2
   Otherthe temperature below 0° C
3. 3
   workup.STIRRINGThe suspension was stirred for a further 30 min
4. 4
   Filtrationfiltered
5. 5
   Washwashed with dried ether

Procedure

A suspension of 3-methoxyaniline (10 g) in concentrated hydrochloric acid (85 ml) was stirred at ca. 0° and a solution of sodium nitrite (5.75 g) in water (25 ml) was slowly added over a period of 30 min keeping the temperature of the mixture at ca. 0°. After 1 h a solution of tin II chloride dihydrate (59 g) in concentrated hydrochloric acid (50 ml) was added over a period of 1.5 h, to the cooled suspension keeping the temperature below 0° C. The suspension was stirred for a further 30 min, filtered and washed with dried ether to give the title compound as a solid (14 g) m.p. 171°.

Source