HCID 54693282, compound → HCID 54717980, compound

HRID 649190Notes

Reaction equation

HRID 649190 reaction equation
[N+]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[C:14](=[O:25])[N:15]([CH3:24])[C:16]3[C:21]([C:22]=2[OH:23])=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:12])=[CH:6][CH:5]=1)([O-])=O>C1(C)C=CC=CC=1>[C:7]1([NH:10][C:11]([C:13]2[C:14](=[O:25])[N:15]([CH3:24])[C:16]3[C:21]([C:22]=2[OH:23])=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:9][CH:8]=1.[N:15]1[CH:16]=[CH:21][CH:22]=[CH:13][CH:14]=1

Participants

3

Reactant 1

HCID 54693282HCID 54693282, compound

Product 1

HCID 54717980HCID 54717980, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture consisting of 34.5 parts of N-(4-nitrophenyl)-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-quinoline-3-carboxamide (1:20), 0.3 parts of platinic oxide, and 330 parts of toluene is hydrogenated at 50° C. and at 5 atm. The catalyst is filtered off and the filtrate is evaporated to dryness in vacuo. The residue crystallizes to give N-(4-aminophenyl)-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-quinoline-3-carboxamide (1). M.p. 300° C.

Workup

  1. customis hydrogenated at 50° C. and at 5 atm
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated to dryness in vacuo
  4. customThe residue crystallizes

Sources & evidence

ORD record
ord-b65352cc0a0a4ce0b1d35c7cfc83eef3
Source dataset
uspto-grants-1988_04
Patent number
US04738971

Reaction notes

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