N-methyl-N-methyloxy-2-benzyloxycarbonylamino-5-methyloxy-benzamide → Benzamide, 2-amino-N,5-dimethoxy-N-methyl-

HRID 275859Notes

Reaction equation

HRID 275859 reaction equation
[CH3:1][N:2]([O:24][CH3:25])[C:3](=[O:23])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[NH:12]C(OCC1C=CC=CC=1)=O>C(OCC)(=O)C.CO.[H][H].[C].[Pd]>[CH3:1][N:2]([O:24][CH3:25])[C:3](=[O:23])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[NH2:12]

Participants

6

Reactant 1

HCID 18315335N-methyl-N-methyloxy-2-benzyloxycarbonylamino-5-methyloxy-benzamide

Product 1

HCID 11514001Benzamide, 2-amino-N,5-dimethoxy-N-methyl-Yield 104.2%

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

In a mixture of ethyl acetate (8 ml) and methanol (10 ml) was dissolved N-methyl-N-methyloxy-2-benzyloxycarbonylamino-5-methyloxy-benzamide (0.55 g). To the solution was added 10% palladium-carbon (0.1 g). The mixture was stirred for 40 minutes at ordinary temperature under atmospheric pressure in hydrogen streams. The reaction mixture was subjected to filtration, and the filtrate was concentrated under reduced pressure. From the concentrate, N-methyl-N-methyloxy 2-amino-5-methyloxy-benzamide (0.35 g) was obtained.

Workup

  1. filtrationThe reaction mixture was subjected to filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3151efb2da3b49d0be0a0571a2d3f433
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

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