Synthesis of succinanilic acid

Preparation of succinanilic acid (N-phenylsuccinamic acid; N-phenylbutanedioic acid monoamide)

Preparation of succinanilic acid (N-phenylsuccinamic acid; N-phenylbutanedioic acid monoamide)

Preparation of succinanilic acid (N-phenylsuccinamic acid; N-phenylbutanedioic acid monoamide)

10 grams of succinic anhydride are dissolved in 30 ml of warm benzene. The solution is heated and  a mixture of 9 ml of aniline in 50 ml of benzene are added. The reaction proceeds very quickly and succinanilic acid separates as white solid. The mixture is cooled, the crystals are collected by filtration, washed with small amount of benzene and dried. Crude succinanilic acid is purified by crystallization from benzene, yielding a white needles, with the melting point of 150° C. Succinanilic acid is also soluble in alcohol, ether, in boiling water (with some decomposition).

Experiments in Organic Chemistry, L. F. Fieser, 105, 1941;

Ann. 162, 176 (1872);

IUPAC Name

4-anilino-4-oxobutanoic acid

InChI

InChI=1S/C10H11NO3/c12-9(6-7-10(13)14)11-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,11,12)(H,13,14)

InChI Key

KTFGFGGLCMGYTP-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)NC(=O)CCC(=O)O

Depositor-Supplied Synonyms

Succinanilic acid, N-Phenylsuccinamic acid, Succinic acid monoanilide, Succinic monoanilide, 102-14-7, 4-Oxo-4-(phenylamino)butanoic acid, N-Phenyl-succinamic acid, N-Phenylbutanedioic acid monoamide, BUTANOIC ACID, 4-OXO-4-(PHENYLAMINO)-, 4-Oxo-4-phenylaminobutanoic acid, Succinamic acid, N-phenyl-, 4-Anilino-4-oxobutanoic acid, CHEMBL152730, 3-(phenylcarbamoyl)propanoic acid, NSC56471, NSC 56471, Propionic acid, 3-(phenylcarbamoyl)-, BRN 2806264, 3-(N-phenylcarbamoyl)propanoic acid, Maybridge1_006842, ChemDiv2_000397, AC1L1P4J, Oprea1_388074, Oprea1_552059, SCHEMBL94252, UNII-L4V0G8222E, 4-anilino-4-oxo-butanoic acid, ARONIS018275, CTK4A0735, HMS560O22, KTFGFGGLCMGYTP-UHFFFAOYSA-N, MolPort-000-385-121, HMS1370C01, L4V0G8222E, AC1Q7569, 4-(phenylamino)-4-oxobutanoic acid, CCG-44906, NSC-56471, SBB006920, STK018310, AKOS000296139, Butanoic acid,4-oxo-4-(phenylamino)-, MCULE-2207328919, AJ-10654, AK-97049, BAS 00281092, LS-46387, ST058108, KB-239128, KB-296421, FT-0662224, A-2174, 4-12-00-00468 (Beilstein Handbook Reference), I04-5396, SR-01000418000-2, T5605179, F0722-4214, F1097-0015

Removed Synonyms

CID7598

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