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

HRID 484257Notes

Reaction equation

HRID 484257 reaction equation
[N:1]([O-])=O.[Na+].[CH2:5]([O:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O.O.[Cl:22][Sn]Cl>>[ClH:22].[CH2:5]([O:12][C:13]1[CH:14]=[CH:15][C:16]([NH:17][NH2:1])=[CH:18][CH:19]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 228604-BenzyloxyanilineHCID 61436Stannous chloride dihydrateHCID 23668193Sodium Nitrite

Product 1

HCID 3016725(4-(Benzyloxy)phenyl)hydrazine monohydrochlorideYield 95%

Procedure

A solution of sodium nitrite (3.8 g, 0.055 mol in 20 mL of H2O), is added dropwise to an ice cold stirring suspension of 4-benzyloxyaniline (13.0 g, 0.055 mol in 150 mL of concentrated HCl). The reaction mixture is stirred for 90 minutes at -8° to 10° C. A solution of SnCl2.2H2O (32.0 g, 0142 mol in 50 mL concentrated HCl) is added and stirred for 1 hour at 0° C. The reaction mixture is removed from the ice bath and is stirred at room temperature for 20 hours. The mixture is then filtered and washed with water to give 13.0 g (95% yield) of product, m.p. 182°-185° C.

Workup

  1. stirringThe reaction mixture is stirred for 90 minutes at -8° to 10° C
  2. stirringstirred for 1 hour at 0° C
  3. customThe reaction mixture is removed from the ice bath
  4. stirringis stirred at room temperature for 20 hours
  5. filtrationThe mixture is then filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-30d0c49e829f4729899f016cfee1232e
Source dataset
uspto-grants-1993_07
Patent number
US05229516

Reaction notes

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