Itaconic acid → trans-N-Octyl-2-[4-(4-carboxy-2-oxo-pyrrolidino)phenyl]cyclopropanecarboxamide

HRID 66799Notes

Reaction equation

HRID 66799 reaction equation
[CH2:1]([NH:9][C:10]([C@@H:12]1[CH2:14][C@H:13]1[C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1)=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:22]([OH:30])(=[O:29])[C:23]([CH2:25][C:26](O)=[O:27])=[CH2:24]>>[CH2:1]([NH:9][C:10]([C@@H:12]1[CH2:14][C@H:13]1[C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:24][CH:23]([C:22]([OH:30])=[O:29])[CH2:25][C:26]2=[O:27])=[CH:17][CH:16]=1)=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

3

Reactant 2

HCID 811Itaconic acidHCID 12854635trans-N-octyl-2-(4-aminophenyl)cyclopropanecarboxamide

Product 1

HCID 54190593trans-N-Octyl-2-[4-(4-carboxy-2-oxo-pyrrolidino)phenyl]cyclopropanecarboxamide

Procedure

A mixture of 2.2 g. of trans-N-octyl-2-(4-aminophenyl)cyclopropanecarboxamide and 989 mg. of itaconic acid were heated as a melt at 140°-145° C. for 1 hour. The reaction mixture was cooled slightly and then it was triturated with 25 ml. of ethyl acetate. The white solid which formed was filtered off. It was recrystallized from ethanol containing a small amount of acetonitrile, and then from acetic acid, to give 1.09 g. of the title compound as a white solid, m.p. 213.5°-214.5° C. The infrared spectrum (KBr disc) showed absorptions at 3280, 3125, 1695 and 1625 cm1.

Workup

  1. additionA mixture of 2.2 g
  2. temperatureThe reaction mixture was cooled slightly
  3. customit was triturated with 25 ml
  4. customThe white solid which formed
  5. filtrationwas filtered off
  6. customIt was recrystallized from ethanol containing a small amount of acetonitrile
  7. customfrom acetic acid, to give 1.09 g

Sources & evidence

ORD record
ord-dcf0a1f93fe9453caa4d461981582f3e
Source dataset
uspto-grants-1982_08
Patent number
US04343813

Reaction notes

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