(3,5-Dimethyl-4-nitrophenyl)(morpholino)methanone → (4-Amino-3,5-dimethylphenyl)(morpholino)methanone

HRID 237522Notes

Reaction equation

HRID 237522 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:13])[CH:5]=[C:6]([CH3:11])[C:7]=1[N+:8]([O-])=O.[H][H]>[Pd].CO>[NH2:8][C:7]1[C:6]([CH3:11])=[CH:5][C:4]([C:12]([N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)=[O:13])=[CH:3][C:2]=1[CH3:1]

Participants

5

Reactant 2

HCID 86697183(3,5-Dimethyl-4-nitrophenyl)(morpholino)methanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 86697184(4-Amino-3,5-dimethylphenyl)(morpholino)methanone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on carbon (100 mg) is added to a solution of (3,5-dimethyl-4-nitrophenyl)(morpholino)methanone (1.3 g) in methanol (10 mL) and the mixture is hydrogenated for 3 hours under 2 bar hydrogen pressure. Then the catalyst is filtered off and washed with methanol. The combined mother liquors are concentrated to give the title compound. Yield: 1.1 g; LC (method 20): tR=1.94; Mass spectrum (ESI+): m/z=235 [M+H]+.

Workup

  1. filtrationThen the catalyst is filtered off
  2. washwashed with methanol
  3. concentrationThe combined mother liquors are concentrated

Sources & evidence

ORD record
ord-5e030e938028466f997ced4f6c548f7e
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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