Hydrochloric Acid → p-(2,4-Dimethoxybenzyloxy)phenyl hydrazine hydrochloride

HRID 1448443Notes

Reaction equation

HRID 1448443 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:4]=1[CH2:5][O:6][C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=1.[N:20]([O-])=O.[Na+].[ClH:24]>O>[ClH:24].[CH3:1][O:2][C:3]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:4]=1[CH2:5][O:6][C:7]1[CH:13]=[CH:12][C:10]([NH:11][NH2:20])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 20379808p-(2,4-Dimethoxybenzyloxy)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 20379814p-(2,4-Dimethoxybenzyloxy)phenyl hydrazine hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

p-(2,4-Dimethoxybenzyloxy)aniline (2.5 g, 0.01 M) is diazotized with concentrated hydrochloric acid (6 ml) and sodium nitrite (1 g) in water (2 ml) at 0° C. This solution is treated with stannous chloride dihydrate (7 g) in concentrated hydrochloric acid (20 ml) at 0° C. for 2 hours. After 12 hours at 0° C. the precipitate is filtered off and recrystallized from ethanol to afford p-(2,4-dimethoxybenzyloxy)phenyl hydrazine hydrochloride. The free base is liberated by treatment with aqueous sodium carbonate and extraction into chloroform.

Workup

  1. filtrationAfter 12 hours at 0° C. the precipitate is filtered off
  2. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-c93b4e10f92745b58adda0de1db6b3b0
Source dataset
uspto-grants-1979_12
Patent number
US04180509

Reaction notes

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