N-(4-methoxycarbonylamino-2-nitrophenyl)-2-dimethylaminoacetamide → N-(2-amino-4-methoxycarbonylaminophenyl)-2-dimethylaminoacetamide

HRID 1415650Notes

Reaction equation

HRID 1415650 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:18])[CH2:14][N:15]([CH3:17])[CH3:16])=[C:8]([N+:19]([O-])=O)[CH:7]=1)=[O:4].[H][H]>[Pt]=O.CO>[NH2:19][C:8]1[CH:7]=[C:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[CH:11]=[CH:10][C:9]=1[NH:12][C:13](=[O:18])[CH2:14][N:15]([CH3:17])[CH3:16]

Participants

5

Reactant 2

HCID 21483074N-(4-methoxycarbonylamino-2-nitrophenyl)-2-dimethylaminoacetamideHCID 178418361HCID 178418361, compound2×

Product 1

HCID 21483024N-(2-amino-4-methoxycarbonylaminophenyl)-2-dimethylaminoacetamideYield 69%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

N-(4-methoxycarbonylamino-2-nitrophenyl)-2-dimethylaminoacetamide (25.3 g), platinum oxide (0.4 g) and methanol (250 ml) were shaken together in an atmosphere of hydrogen at atmospheric pressure and laboratory temperature until the uptake of hydrogen was complete. Six litres of hydrogen were absorbed. The mixture was filtered and the ethanol evaporated. The residual solid was recrystallised from isopropanol to give N-(2-amino-4-methoxycarbonylaminophenyl)-2-dimethylaminoacetamide (15.7 g), m.p. 140°-142° C.

Workup

  1. customSix litres of hydrogen were absorbed
  2. filtrationThe mixture was filtered
  3. customthe ethanol evaporated
  4. customThe residual solid was recrystallised from isopropanol

Sources & evidence

ORD record
ord-1d2cde70f0ec4f03900342fcf15a6a84
Source dataset
uspto-grants-1977_01
Patent number
US04005217

Reaction notes

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