Maleic Anhydride → Luminol maleamic acid

HRID 745847Notes

Reaction equation

HRID 745847 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:4]([C:5](NN)=[O:6])[C:3]=1[C:12]([NH:14][NH2:15])=[O:13].[C:16]1(=[O:22])[O:21][C:19](=[O:20])[CH:18]=[CH:17]1>C(O)(=O)C>[CH:10]1[CH:11]=[C:2]([NH2:1])[C:3]2[C:12]([NH:14][NH:15][C:5](=[O:6])[C:4]=2[CH:9]=1)=[O:13].[C:16]([OH:21])(=[O:22])/[CH:17]=[CH:18]\[C:19]([NH2:1])=[O:20]

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 2455213-Aminobenzene-1,2-dicarbohydrazide

Product 1

HCID 131714781Luminol maleamic acidYield 147.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1.77 grams (0.01 mol) of 3-amino phthalhydrazide and 1.5 grams of maleicanhydride in 10 milliliters of acetic acid was stirred at ambient temperature for 2 hours. The reddish product was filtered and washed with ether. 2.15 grams of luminol-maleamic acid was obtained. IR (KBR) showed bands at 3100; 3020; 2940; 2920; 2600; 1720; 1703; 1650; 1630; 1592; 1560; 1528; 1492; 1460; 1330; 1300; 1285; 1230; 1180 and 1120 cm-1.

Workup

  1. filtrationThe reddish product was filtered
  2. washwashed with ether

Sources & evidence

ORD record
ord-afdcda348d5c4fec80cf23f0c281f2e1
Source dataset
uspto-grants-1986_07
Patent number
US04600775

Reaction notes

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