Isopropanol → Acetic acid, (p-aminobenzoyl)-, ethyl ester (6CI,7CI)

HRID 34895

Reaction equation

HRID 34895 reaction equation
[Cl-].[NH4+].C(O)(C)C.[N+:7]([C:10]1[CH:23]=[CH:22][C:13]([C:14]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:15])=[CH:12][CH:11]=1)([O-])=O>O>[NH2:7][C:10]1[CH:11]=[CH:12][C:13]([C:14]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:15])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 13281Benzenepropanoic acid, 4-nitro-beta-oxo-, ethyl esterHCID 25517Ammonium Chloride

Product 1

HCID 3045879Acetic acid, (p-aminobenzoyl)-, ethyl ester (6CI,7CI)Yield 83.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

Into a mixture comprising 224 g of reduced iron, 13.4 g of ammonium chloride, 1 liter of isopropyl alcohol and 0.2 liter of water was added 237 g of ethyl p-nitrobenzoylacetate in small portions at a temperature between 50° C. and 70° C. with caution against heat generation. The mixture was allowed to react at 70° C. for 1 hour, followed by filtration. To the filtrate was added 1 liter of water, and crystals precipitated upon cooling to 5° C. were separated by filtration to obtain 172 g of ethyl p-aminobenzoylacetate as yellow crystals having a melting point of 82° to 84° C.

Workup

  1. temperatureagainst heat generation
  2. customto react at 70° C. for 1 hour
  3. filtrationfollowed by filtration
  4. additionTo the filtrate was added 1 liter of water, and crystals
  5. customprecipitated
  6. customwere separated by filtration

Sources & evidence

ORD record
ord-70063811dc024232a0f27156d70ecbb3
Source dataset
uspto-grants-1988_08
Patent number
US04764458

Linked notes

Loading…