Methyl 3-(aminocarbonyl)-4-nitrobenzoate → 63746-27-0

HRID 2286871Notes

Reaction equation

HRID 2286871 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-])=O)=[C:9]([CH:13]=1)[C:10]([NH2:12])=[O:11])=[O:4]>CO.[Pd]>[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:9]([C:10]([NH2:12])=[O:11])[C:8]([NH2:14])=[CH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 1

HCID 23460476Methyl 3-(aminocarbonyl)-4-nitrobenzoate

Product 1

HCID 1334196363746-27-0

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-Methoxycarbonyl-2-nitrobenzamide (28 g.) was dissolved in methanol (600 ml.), 10% palladium-on-charcoal catalyst (3 g.) was added, and the mixture was hydrogenated for 6 hours at about 35° C. The catalyst was filtered off, extracted with methanol (350 ml.) at reflux temperature under an atmosphere of nitrogen for 20 minutes, and filtered again. Both filtrates were evaporated to dryness, and the combined residues were crystallised from water (3 l.) to give 5-methoxycarbonylanthranilamide, m.p. 188°-193° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. extractionextracted with methanol (350 ml.)
  3. temperatureat reflux temperature under an atmosphere of nitrogen for 20 minutes
  4. filtrationfiltered again
  5. customBoth filtrates were evaporated to dryness
  6. customthe combined residues were crystallised from water (3 l.)

Sources & evidence

ORD record
ord-27927e30bfe3469e9e5ffc4ade7d111a
Source dataset
uspto-grants-1981_05
Patent number
US04268510

Reaction notes

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