Hydrazine hydrate (1:1) → 2-Benzyloxyaniline

HRID 1198519Notes

Reaction equation

HRID 1198519 reaction equation
O.NN.[CH2:4]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-])=O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>[Ni].CO>[CH2:4]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH2:18])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 736266Benzyl 2-nitrophenyl ether

Product 1

HCID 2405482-Benzyloxyaniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Hydrazine hydrate (5 ml) was added dropwise over 20 minutes to a stirred suspension of Raney nickel in a solution of 2-(benzyloxy)nitrobenzene in methanol (200 ml) causing gentle reflux. The stirred mixture was heated under reflux for a further 30 minutes, cooled, filtered and evaporated. The residue was distilled under vacuum to give a pale oil, b.p. 146°-150°/0.5 mm.

Workup

  1. temperatureThe stirred mixture was heated
  2. temperatureunder reflux for a further 30 minutes
  3. temperaturecooled
  4. filtrationfiltered
  5. customevaporated
  6. distillationThe residue was distilled under vacuum
  7. customto give a pale oil, b.p. 146°-150°/0.5 mm

Sources & evidence

ORD record
ord-1b4d72a7a0de49db86d1f48e2d7f03be
Source dataset
uspto-grants-1994_01
Patent number
US05281593

Reaction notes

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