Maleic Anhydride → HCID 67562912, compound

HRID 1417356Notes

Reaction equation

HRID 1417356 reaction equation
Cl.[NH2:2][C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1.[C:14]1(=[O:20])[O:19][C:17](=[O:18])[CH:16]=[CH:15]1.C(N(CC)CC)C>ClCCl>[C:9](/[CH:8]=[CH:7]/[C:6]1[CH:5]=[CH:4][C:3]([NH:2][C:14](=[O:20])/[CH:15]=[CH:16]\[C:17]([OH:19])=[O:18])=[CH:13][CH:12]=1)([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 7923Maleic AnhydrideHCID 8471TriethylamineHCID 1038662-Propenoic acid, 3-(4-aminophenyl)-, hydrochloride

Product 1

HCID 67562912HCID 67562912, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The method of Example 1 was employed using 4-aminocinnamic acid hydrochloride (10.0 g, 0.0501 mol) and maleic anhydride (5.00 g, 0.0509 mol). Triethylamine (7.00 ml, 0.0502 mol) in dichloromethane (100 ml) was added to generate the free amine. The yellow maleamic acid was obtained. H.p.l.c. 100%. 1H-n.m.r. (DMSO): δ 10.51 (1H, s, NH); 7.65 (4H, bs, ar H's); 7.55 (1H, d, pH-CH); 6.44 (2H, t, HO2C CH=CH; CO, PhCH=CH); 6.30 (1H, d, HO2C CH=CH CO).

Sources & evidence

ORD record
ord-1ab8b90630b3438ea2819424a7e9204f
Source dataset
uspto-grants-1999_03
Patent number
US05877204

Reaction notes

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