Ethanol → Ethyl 4-(acetylamino)-3-aminobenzoate

HRID 2229448Notes

Reaction equation

HRID 2229448 reaction equation
[C:1]([NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([O-:11])=[O:10])=[CH:7][C:6]=1[N+:14]([O-])=O)(=[O:3])[CH3:2].[CH2:17](O)[CH3:18].[H][H]>[Pd].O>[C:1]([NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([O:11][CH2:17][CH3:18])=[O:10])=[CH:7][C:6]=1[NH2:14])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 702EthanolHCID 46327374-Acetamido-3-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 12051751Ethyl 4-(acetylamino)-3-aminobenzoateYield 40.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

A mixture of wet crystals of 4-(acetylamino)-3-nitrobenzoate (45.3 g, purity: 66.2%), ethanol (191.6 g), water (31.9 g), and palladium-on-carbon (palladium content: 5%, water content: 50%, 3.0 g) was stirred at 40° C. for 19 hours at a hydrogen atmosphere. The catalyst was collected by filtration and washed with a mixed solvent of water and ethanol (1/9, 30.0 g). The filtrate was concentrated, and t-butyl methyl ether (33.0 g) was added dropwise thereto at 50° C., and the mixture was cooled to 10° C. to effect crystallization. Crystals were collected and washed with t-butyl methyl ether (30.0 g), and dried at 60° C. under reduced pressure. Thus, ethyl 4-(acetylamino)-3-aminobenzoate (18.2 g) was obtained.

Workup

  1. filtrationThe catalyst was collected by filtration
  2. washwashed with a mixed solvent of water and ethanol (1/9, 30.0 g)
  3. concentrationThe filtrate was concentrated
  4. additiont-butyl methyl ether (33.0 g) was added dropwise
  5. customcrystallization
  6. customCrystals were collected
  7. washwashed with t-butyl methyl ether (30.0 g)
  8. customdried at 60° C. under reduced pressure

Sources & evidence

ORD record
ord-c6cf43a21148409ba19272618c63c894
Source dataset
uspto-grants-2002_07
Patent number
US06420409B1

Reaction notes

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