4-(4-Aminophenyl)-4-oxobutanoic acid → 3-[p-(1-Chlorocyclopropylcarbonylamino)-benzoyl]-propionic acid

HRID 647808

Reaction equation

HRID 647808 reaction equation
[Cl:1][C:2]1([C:5](Cl)=[O:6])[CH2:4][CH2:3]1.[NH2:8][C:9]1[CH:21]=[CH:20][C:12]([C:13]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[O:14])=[CH:11][CH:10]=1>O1CCCC1>[Cl:1][C:2]1([C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([C:13]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[O:14])=[CH:20][CH:21]=2)=[O:6])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 2432904-(4-Aminophenyl)-4-oxobutanoic acidHCID 10942508Cyclopropanecarbonyl chloride, 1-chloro-

Product 1

HCID 204833713-[p-(1-Chlorocyclopropylcarbonylamino)-benzoyl]-propionic acidYield 49.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.9 g (28.1 millimoles) of 1-chlorocyclopropanecarboxylic acid chloride are added, with stirring, to 4.5 g (23.3 millimoles) of 3-(p-aminobenzoyl)-propionic acid in 100 ml of absolute tetrahydrofuran. The reaction mixture is then stirred for 20 hours at room temperature, followed by 7 hours under reflux. A small amount of solid is filtered off and discarded, and the filtrate is concentrated. The residue obtained is recrystallized from ethyl acetate, giving 3.4 g (49% of theory) of 3-[p-(1-chlorocyclopropylcarbonylamino)-benzoyl]-propionic acid as colorless crystals, of melting point 178°-179° C.

Workup

  1. waitfollowed by 7 hours
  2. temperatureunder reflux
  3. filtrationA small amount of solid is filtered off
  4. concentrationthe filtrate is concentrated
  5. customThe residue obtained
  6. customis recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-74d38cc0253c41d886bfa8b64df79659
Source dataset
uspto-grants-1983_10
Patent number
US04410529

Linked notes

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