Phthalic Anhydride → Fluorescein phthalamic acid

HRID 745849Notes

Reaction equation

HRID 745849 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:37])[O:32][C:30](=[O:31])[C:29]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:28]12>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:37])[C:28]1[C:29](=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:30]([NH2:7])=[O:31]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 768455-Aminofluorescein

Product 1

HCID 131714783Fluorescein phthalamic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 350 mg (0.001 mol) of 5-aminofluorescein and 200 mg of phthalic anhydride in 5 milliliters of glacial acetic acid was stirred at ambient temperature for 48 hours. The yellow reddish product was filtered and washed once with acetic acid and twice with diethyl ether. 460 Mg of fluorescein-phthalamic acid was obtained. I.R (KBR) showed bands at 3060; 3000; 1685; 1590; 1540; 1480; 1460; 1430; 1350; 1310; 1270; 1230; 1195; 1150; and 1115 cm-1.

Workup

  1. filtrationThe yellow reddish product was filtered
  2. washwashed once with acetic acid and twice with diethyl ether

Sources & evidence

ORD record
ord-7cbb0db406bd487cad6863495797162b
Source dataset
uspto-grants-1986_07
Patent number
US04600775

Reaction notes

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