HCID 54423379, compound → HCID 54118816, compound

HRID 1679920Notes

Reaction equation

HRID 1679920 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C@H:8]2[CH2:10][C@H:9]2[C:11]([OH:13])=[O:12])=[O:7])=[CH:4][CH:3]=1>C(OC(=O)CC)(=O)CC>[C:6]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C@H:8]2[CH2:10][C@H:9]2[C:11]([OH:13])=[O:12])=[O:7])=[CH:14][CH:15]=1)(=[O:7])[CH2:5][CH3:4]

Participants

3

Reactant 1

HCID 54423379HCID 54423379, compound

Product 1

HCID 54118816HCID 54118816, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 31263Propionic anhydrideSolvent

Procedure

5.0 g (24.4 millimoles) of cis-2-(p-aminobenzoyl)-cyclopropanecarboxylic acid (see Example 9a) and 50 ml of propionic anhydride are kept at 80° C. for 30 minutes. The solution is then poured into ice water. The oil which hereupon separates out is left to stand overnight at room temperature in the aqueous phase, during which time it solidifies. It is then filtered off, washed with water and recrystallized from ethyl acetate/petroleum ether. 1.9 g (30% of theory) of cis-2-(p-propionylaminobenzoyl)-cyclopropanecarboxylic acid are isolated as colorless crystals of melting point 182°-183° C.

Workup

  1. waitThe oil which hereupon separates out is left
  2. filtrationIt is then filtered off
  3. washwashed with water
  4. customrecrystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-3fc5b0aba8744fbf9ec84fea5df0bff1
Source dataset
uspto-grants-1981_06
Patent number
US04271163

Reaction notes

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