Synthesis of 4-nitroacetanilide (para-nitroacetanilide)

Preparation of 4-nitroacetanilide

Preparation of 4-nitroacetanilide

Preparation of 4-nitroacetanilide

100 g of acetanilide are dissolved in 167 ml of sulfuric acid contained in a round flask, the temperature not being allowed to rise above 40° C. The solution is cooled to 5-10° C with ice-water, and the cooled mixture of 44 ml of nitric acid with 28 ml of sulfuric acid is added very slowly. During the addition the reaction mixture is stirred and cooled in the ice-water, the temperature being kept below 15° C. After standing a short time, the nitration mixture is poured into about 10 liters of water containing several lumps of ice, when the 4-nitroacetanilide separates out, and is filtered, washed properly from acids, and dried. 4-Nitroacetanilide is further purified by crystallization from ethanol yielding 110-120 g of almost colorless needles with melting point 207° C. The side product 2-nitroacetanilide is removed by extracting with chloroform, in which the 2-nitroacetanilide is soluble.

The Synthetic Dyestuffs and the Intermediate Products from which They are Derived, by J. C. Cain, 202, 1905

IUPAC Name

N-(4-nitrophenyl)acetamide

InChI

InChI=1S/C8H8N2O3/c1-6(11)9-7-2-4-8(5-3-7)10(12)13/h2-5H,1H3,(H,9,11)

InChI Key

NQRLPDFELNCFHW-UHFFFAOYSA-N

Canonical SMILES

CC(=O)NC1=CC=C(C=C1)[N+](=O)[O-]

MeSH Synonyms

4-nitroacetanilide

Depositor-Supplied Synonyms

4′-Nitroacetanilide, N-(4-Nitrophenyl)acetamide, 4-NITROACETANILIDE, 104-04-1, P-Nitroacetanilide, N-Acetyl-4-nitroaniline, p-Acetamidonitrobenzene, Acetamide, N-(4-nitrophenyl)-, Acetanilide, p-nitro-, p-Nitrophenylacetanilide, N-Acetyl-p-nitroaniline, Acetanilide, 4′-nitro-, NSC 1315, Acetic acid 4-nitroanilide, CCRIS 5566, NQRLPDFELNCFHW-UHFFFAOYSA-N, EINECS 203-169-0, SBB058050, AI3-01545, 68239-25-8, Acetamide, N-(4-nitrophenyl-2,3,5,6-d4)-, nitroacetanilide, p-acetamino nitrobenzene, AC1Q5MEP, Maybridge1_001346, WLN: WNR DMV1, N-(p-Nitrophenyl)acetamide, 4-(Acetylamino)nitrobenzene, AC1L1PC3, N-Acetyl-4-nitrobenzenamine, ACMC-1C41B, 1-Nitro-4-acetylaminobenzene, N-(4-nitrophenyl)-acetamide, ARONIS23973, SCHEMBL642700, 130648_ALDRICH, ARONIS023787, CHEMBL131469, UNII-PH3B066365, CTK2F4289, HMS545F04, NSC1315, Acetanilide, 4′-nitro- (8CI), MolPort-000-860-875, N-(4-nitrophenyl)ethanimidic acid, NSC-1315, ANW-15019, AR-1G3926, LABOTEST-BB LT00455738, LABOTEST-BB LT03330920, STK004304, ZINC16321384, AKOS003237246, AS00883, MCULE-4712987402, PH3B066365, VZ27409, AJ-68853, AK116555, AN-24667, LS-10807, DB-040507, KB-193589, ST2419665, FT-0619197, N0108, ST45053120, ST50405710, I01-7155, 1-Nitro-4-acetylaminobenzene;N-(4-nitrophenyl)acetamide, 3B3-013322

Removed Synonyms

CID7691, A1894, 6929-42-6

Share This

Leave a Reply

Your email address will not be published. Required fields are marked *