Ethanol → HCID 21954977, compound

HRID 2095162Notes

Reaction equation

HRID 2095162 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1.C(O)C.O.NN>C1COCC1.[Ni]>[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1

Participants

6

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 1238782HCID 1238782, compound

Product 1

HCID 21954977HCID 21954977, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-methoxy-5-nitrobenzyl)morpholine (252 mg, 1.0 mmol) in THF:ethanol mixture (1:1) (25 mL) was added a catalytical amount of Raney-Nickel and hydrazine hydrate (450 mg; 9.0 mmol) and the mixture was stirred for 1 hour at ambient temperature, filtered through a Celite/silica gel pad. The filtrate was evaporated to yield the pure 4-methoxy-3-morpholin-4-ylmethylphenylamine (149 mg, 67%), which was used in the next step without purification.

Workup

  1. filtrationfiltered through a Celite/silica gel pad
  2. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-6aaede55d95b4e1bba19d845a9055881
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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