Maleic Anhydride → Fluorescein maleamic acid

HRID 414113

Reaction equation

HRID 414113 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][C:4]2[C:8]([O:10][C:11]3([C:21]4[CH:22]=[CH:23][C:24]([OH:26])=[CH:25][C:20]=4[O:19][C:13]4[CH:14]=[C:15]([OH:18])[CH:16]=[CH:17][C:12]3=4)[C:3]=2[CH:2]=1)=[O:9].[C:27]1(=[O:33])[O:32][C:30](=[O:31])[CH:29]=[CH:28]1>C(O)(=O)C>[CH:1]1[CH:6]=[CH:5][C:4]([C:8]([OH:10])=[O:9])=[C:3]([C:11]2[C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]=3[O:19][C:20]3[C:21]=2[CH:22]=[CH:23][C:24]([CH:25]=3)=[O:26])[CH:2]=1.[C:27]([OH:32])(=[O:33])/[CH:28]=[CH:29]\[C:30]([NH2:7])=[O:31]

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 768455-Aminofluorescein

Product 1

HCID 131714782Fluorescein maleamic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 350 milligrams (0.001 mols) of 5-aminofluorescein and 300 milligrams (excess) of maleic anhydride were mixed in 5.0 milliliters of glacial acetic acid and the mixture was stirred at ambient temperature for 24 hours. The yellow product formed was filtered off and washed three times with diethyl ether. 420 Milligrams of fluorescein-maleamic acid was obtained. l.R (KBR) showed bands at 2.55; 3.28; 3.38; 4.05; 5.85; 6.30; 6.52; 6.88; 6.90; 7.70; 8.34; 8.52; and 8.30μ.

Workup

  1. customThe yellow product formed
  2. filtrationwas filtered off
  3. washwashed three times with diethyl ether

Sources & evidence

ORD record
ord-b693c34ebc68434d90b4e182d77e498e
Source dataset
uspto-grants-1988_12
Patent number
US04789742

Linked notes

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