Hydrazine hydrate (1:1) → 5-Benzyloxy-2-fluoro-4-methylaniline

HRID 393592

Reaction equation

HRID 393592 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH3:19])=[CH:11][C:12]([F:18])=[C:13]([N+:15]([O-])=O)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>CO.[Ni]>[CH2:1]([O:8][C:9]1[C:10]([CH3:19])=[CH:11][C:12]([F:18])=[C:13]([CH:14]=1)[NH2:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 219910575-Benzyloxy-2-fluoro-4-methylnitrobenzene

Product 1

HCID 219910685-Benzyloxy-2-fluoro-4-methylanilineYield 100.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent2×

Procedure

5-Benzyloxy-2-fluoro-4-methyl-1-nitrobenzene (500 mg, 1.9 mmol) in methanol (110 ml) was added to a suspension of Raney nickel (75 mg) and hydrazine hydrate (0.47 ml, 9.5 mmol) in methanol (10 ml) and heated at reflux. The mixture was maintained under reflux for 15 minutes and then the insoluble materials removed by filtration through diatomaceous earth. The filter pad was washed with methanol and the solvent removed from the filtrate by evaporation to give 5-benzyloxy-2-fluoro-4-methylaniline (440 mg, 99%).

Workup

  1. temperatureheated
  2. temperatureat reflux
  3. temperatureThe mixture was maintained
  4. temperatureunder reflux for 15 minutes
  5. customthe insoluble materials removed by filtration through diatomaceous earth
  6. washThe filter pad was washed with methanol
  7. customthe solvent removed from the filtrate by evaporation

Sources & evidence

ORD record
ord-cfc0ceaa331d4cb68eb0530bf25929f4
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Linked notes

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