4-Benzyloxyaniline hydrochloride → (4-(Benzyloxy)phenyl)hydrazine monohydrochloride

HRID 1029729Notes

Reaction equation

HRID 1029729 reaction equation
[ClH:1].[CH2:2]([O:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N:17]([O-])=O.[Na+]>O.Cl>[ClH:1].[CH2:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]([NH:14][NH2:17])=[CH:15][CH:16]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 27238314-Benzyloxyaniline hydrochlorideHCID 23668193Sodium Nitrite

Product 1

HCID 3016725(4-(Benzyloxy)phenyl)hydrazine monohydrochlorideYield 68%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Procedure

p-Benzyloxyphenylhydrazine hydrochloride was prepared by the method of Mentzer, et al., [C.A. 48:33412]. Thus, p-benzyloxyaniline hydrochloride (72.6 g) was diazotized with conc. HCl (174 ml) and sodium nitrite (23.2 g) in water (40 ml) at 0° C. A solution of stannous chloride (169.3 g) in conc. HCl (435 ml) was added rapidly and the reaction mixture stirred for two hours. The solid product was filtered and washed with absolute ethanol, then partially dissolved in boiling methanol/ethanol (1:1) and filtered hot, yielding 52.5 g of p-benzyloxyphenylhydrazine hydrochloride.

Workup

  1. customp-Benzyloxyphenylhydrazine hydrochloride was prepared by the method of Mentzer, et al., [C.A. 48:33412]
  2. filtrationThe solid product was filtered
  3. washwashed with absolute ethanol
  4. dissolutionpartially dissolved
  5. filtrationfiltered hot

Sources & evidence

ORD record
ord-b96e9d1c9341433b95c43113f1d5f2bd
Source dataset
uspto-grants-1992_04
Patent number
US05102891

Reaction notes

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