HCID 20494956, compound → HCID 20494955, compound

HRID 1074863Notes

Reaction equation

HRID 1074863 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:12]2[CH:17]=[C:16]([Cl:18])[C:15](=[O:19])[C:14]([C:20]([O:22][CH3:23])=[O:21])=[C:13]2[CH3:24])[C:7]([CH3:11])=[CH:8][C:9]=1[CH3:10])([O-])=O>CN(C)C=O.[Ni]>[NH2:1][C:4]1[CH:5]=[C:6]([N:12]2[CH:17]=[C:16]([Cl:18])[C:15](=[O:19])[C:14]([C:20]([O:22][CH3:23])=[O:21])=[C:13]2[CH3:24])[C:7]([CH3:11])=[CH:8][C:9]=1[CH3:10]

Participants

4

Reactant 1

HCID 20494956HCID 20494956, compound

Product 1

HCID 20494955HCID 20494955, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6228DimethylformamideSolvent

Procedure

14.7 g (0.042 mol) 1-(3'-nitro-4',6'-dimethylphenyl)-5-chloro-3-methoxycarbonyl-2-methyl-4-pyridone are dissolved in 450 ml dimethylformamide and, after adding of 1.5 g Raney-Ni hydrogenated at normal pressure and 20°-25° C. The catalyst is filtered off and the filtrate is concentrated by evaporation of the solvent. Cristallisation of the residue from ethanol yields 13.2 g (98%) 1-(3'-amino-4',6'-dimethylphenyl)-5-chloro-3-methoxycarbonyl-2-methyl-4-pyridone, mp. 215° C.

Workup

  1. customhydrogenated at normal pressure and 20°-25° C
  2. filtrationThe catalyst is filtered off
  3. concentrationthe filtrate is concentrated by evaporation of the solvent

Sources & evidence

ORD record
ord-7ccbb97c68c9448fbd91cb72d5a4a676
Source dataset
uspto-grants-1983_07
Patent number
US04394156

Reaction notes

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