Maleic Anhydride → Fluorescein maleamic acid

HRID 745848Notes

Reaction equation

HRID 745848 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. 1.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-ec89bd94355a4786b06c363daa5e8ec9
Source dataset
uspto-grants-1986_07
Patent number
US04600775

Reaction notes

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