Hydrochloric Acid → 3-Methoxyphenylhydrazine hydrochloride

HRID 4383

Reaction equation

HRID 4383 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[N:10]([O-])=O.[Na+].[Sn].[ClH:15]>O>[ClH:15].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:6][NH2:10])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 108243-MethoxyanilineHCID 5352426Tin atomHCID 23668193Sodium Nitrite

Product 1

HCID 27239403-Methoxyphenylhydrazine hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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°.

Workup

  1. customat ca. 0°
  2. customthe temperature below 0° C
  3. stirringThe suspension was stirred for a further 30 min
  4. filtrationfiltered
  5. washwashed with dried ether

Sources & evidence

ORD record
ord-f29eda88a35249c99e36ce3a1f68295a
Source dataset
uspto-grants-1988_02
Patent number
US04725615

Linked notes

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