Stannous Chloride → 4-Benzyloxy-2-fluorophenylhydrazine hydrochloride

HRID 392810

Reaction equation

HRID 392810 reaction equation
[N:1]([O-])=O.[Na+].[CH2:5]([O:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[C:15]([F:20])[CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl:21][Sn]Cl>O.Cl>[ClH:21].[CH2:5]([O:12][C:13]1[CH:19]=[CH:18][C:16]([NH:17][NH2:1])=[C:15]([F:20])[CH:14]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 24479Stannous ChlorideHCID 114998094-(Benzyloxy)-2-fluoroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 116375674-Benzyloxy-2-fluorophenylhydrazine hydrochlorideYield 77.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Procedure

A solution of NaNO2 (1.38 g) in H2O (8 mL) was added to a suspension of 4-benzyloxy-2-fluoroaniline (5.0 g) in 6N HCl (24 mL) at 0° C. After 30 minutes stirring, a solution of SnCl2 (7.7 g) in 6N HCl (24 mL) was added to the mixture at 0° C. The mixture was allowed to warm to room temperature and stirred for 1.5 hours to produce a precipitate. The precipitate was collected by filtration to yield 4.15 g of the title compound.

Workup

  1. stirringstirred for 1.5 hours
  2. customto produce a precipitate
  3. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-5fd2936fa3204d8a9f9999cf28a8ea6b
Source dataset
uspto-grants-2004_10
Patent number
US06803372B2

Linked notes

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