4-(4-Benzyloxy-3-nitro-phenyl)-morpholine → 2-amino-4-(4-morpholinyl)Phenol

HRID 1060305Notes

Reaction equation

HRID 1060305 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[CH:11][C:10]=1[N+:21]([O-])=O)C1C=CC=CC=1>ClCCl.C(O)C.[Pd]>[NH2:21][C:10]1[CH:11]=[C:12]([N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[CH:13]=[CH:14][C:9]=1[OH:8]

Participants

5

Reactant 1

HCID 222833454-(4-Benzyloxy-3-nitro-phenyl)-morpholine

Product 1

HCID 222830622-amino-4-(4-morpholinyl)PhenolYield 96%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

Catalytic hydrogenation of 4-(4-benzyloxy-3-nitro-phenyl)-morpholine (5 g, 16 mmol) in dichloromethane (500 ml) and ethanol (500 ml) using palladium on carbon (500 mg, 10%) afforded the title compound as a grey solid (96%), MS: m/e=194(M+).

Sources & evidence

ORD record
ord-f2eac1b4a5f5466e912b072d1194ce74
Source dataset
uspto-grants-2003_02
Patent number
US06521754B2

Reaction notes

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