Maleic Anhydride → HCID 86747142, compound

HRID 2255014Notes

Reaction equation

HRID 2255014 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22].[C:24]1(=[O:30])[O:29][C:27](=[O:28])[CH:26]=[CH:25]1>C(O)C.[OH-].[Na+]>[C:21]([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:24](=[O:30])/[CH:25]=[CH:26]\[C:27]([OH:29])=[O:28])([OH:23])=[O:22]

Participants

5

Reactant 2

HCID 7923Maleic AnhydrideHCID 18477217HCID 18477217, compound

Product 1

HCID 86747142HCID 86747142, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
40 °C

Procedure

In a mixture of 85 ml of ethanol and 40 ml of 1N aqueous sodium hydroxide solution, 20-aminoeicosanoic acid (500 mg, 1.53 mmoles) was dissolved at 40° C. To the obtained solution, while maintained at 40° C., was gradually added maleic anhydride (3.75 g, 38.3 mmoles) over a period of 3 hours. The pH of the reaction mixture was kept at 8-10 during the addition. The reaction mixture was stirred for 30 minutes and then treated in the same manner as in Reference Example 4, to give N-(19-carboxynonadecyl)maleamic acid (538 mg, 83%) having the following properties.

Workup

  1. dissolutionwas dissolved at 40° C
  2. customof 3 hours
  3. additionThe pH of the reaction mixture was kept at 8-10 during the addition
  4. additiontreated in the same manner as in Reference Example 4

Sources & evidence

ORD record
ord-33c5d02ff6ad45e8b23091eddd9b3d47
Source dataset
uspto-grants-1993_08
Patent number
US05238837

Reaction notes

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