Synthesis of 4-nitrophenyloxamic acid

Preparation of 4-nitrophenyloxamic acid

Alternative Names: oxalyl-p-nitroaniline; N-(4-nitrophenyl)oxamic acid; 4′-nitrooxanilic acid

Preparation of 4-nitrophenyloxamic acid (oxalyl-p-nitroaniline; N-(4-nitrophenyl)oxamic acid; 4'-nitrooxanilic acid)

Preparation of 4-nitrophenyloxamic acid (oxalyl-p-nitroaniline; N-(4-nitrophenyl)oxamic acid; 4′-nitrooxanilic acid)

A mixture of finely pulverized of 138 grams (1.0 mole) of p-nitroaniline and 225 grams (2.5 moles) of anhydrous oxalic acid is heated with proper stirring at 110° C. Then the temperature is kept at 100° C over a period of 2 hours, during which time the 4-nitroaniline oxalate is formed. Thereafter the mixture is held at 110° C for 12 hours with continuous stirring. The water formed escapes by evaporation, some oxalic acid being carried over with it. The end of the reaction is recognized from the fact that the reaction mixture becomes water insoluble. When this point is reached, the crude product is stirred with 1.5 liters of cold water, then filtered off from the oxalic acid solution. The precipitate is washed three times on the funnel with 250 ml portions of cold water. The yield of crude p-nitrophenyloxamic acid is about 95% of the theoretical amount. The product melts at 205-207° C, and after recrystallization from water, at 210° C.

The fundamental processes of dye chemistry, by H. E. Fierz-David, 93-94, 1949

IUPAC Name

2-(4-nitroanilino)-2-oxoacetic acid

InChI

InChI=1S/C8H6N2O5/c11-7(8(12)13)9-5-1-3-6(4-2-5)10(14)15/h1-4H,(H,9,11)(H,12,13)

InChI Key

ZEJKSYPGUAUQKW-UHFFFAOYSA-N

Canonical SMILES

C1=CC(=CC=C1NC(=O)C(=O)O)[N+](=O)[O-]

MeSH Synonyms

4-nitrophenyloxamic acid, p-nitrophenyloxamic acid

Depositor-Supplied Synonyms

4-Nitrophenyloxamic acid, 103-94-6, Oxalyl-p-nitroaniline, N-(4-Nitrophenyl)oxamic acid, 4′-Nitrooxanilic acid, OXANILIC ACID, 4′-NITRO-, [(4-nitrophenyl)amino](oxo)acetic acid, EINECS 203-160-1, ((4-Nitrophenyl)amino)oxoacetic acid, NSC 57783, SBB028541, [(4-nitrophenyl)carbamoyl]formic acid, 2-(4-nitroanilino)-2-oxoacetic acid, BRN 2809447, Acetic acid, ((4-nitrophenyl)amino)oxo-, Acetic acid, [(4-nitrophenyl)amino]oxo-, Kyselina N-(4-nitrofenyl)oxamova [Czech], N-(4-nitrophenyl)methanecarboxylic acid, 21704-45-0, Acetic acid, 2-((4-nitrophenyl)amino)-2-oxo-, Acetic acid, 2-[(4-nitrophenyl)amino]-2-oxo-, nitrophenyloxamic acid, AC1L1PBO, AC1Q5MEQ, AC1Q71MY, ACMC-1C8M7, SCHEMBL3189929, CTK3J2954, Kyselina N-(4-nitrofenyl)oxamova, MolPort-000-157-774, KST-1A2755, NSC57783, AR-1A8391, NSC-57783, AKOS009158372, MCULE-2403191345, RTR-000909, VZ29624, KB-72810, LS-99548, DB-040496, TR-000909, FT-0619246, ST50407812, Z-0281, 2-12-00-00392 (Beilstein Handbook Reference), A800856, I04-3458, 2-[(4-nitrophenyl)amino]-2-oxidanylidene-ethanoic acid, 3B3-006170

Removed Synonyms

CID7686

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