Synthesis of 4′-aminoacetanilide

Preparation of 4′-aminoacetanilide

Preparation of 4′-aminoacetanilide

Preparation of 4′-aminoacetanilide

180 g of moist p-nitroacetanilide are added in small portions to a vessel fitted with good agitation, and containing 125 g. iron filings, 8 ml 40% acetic acid and 500 ml water heated to boiling. Boiling is continued for 10 minutes after the last addition, when the solution “spotted ” on filter paper should be colorless. The liquid is then cooled to 70° C, and sodium carbonate is added until the reaction is alkaline (if the sodium carbonate is added at 100 ° C or in excess, hydrolysis of the p-aminoacetanilide takes place). The precipitation of the iron is completed by adding the minimum quantity of ammonium sulfide until a drop on filter paper gives no coloration with sodium sulfide. The obtained reaction mixture is then filtered, and the filtrate evaporated to 400 ml, when, on cooling, the p-aminoacetanilide crystallizes in long needles. A further crop of crystals may be obtained by evaporating the mother liquor. Yield. 55% theoretical (80-90 g.). m.p. 162.5°; on hydrolysis gives p-phenylenediamine.

Systematic organic chemistry, by W. M. Cumming, 360-361, 1937.





InChI Key


Canonical SMILES


MeSH Synonyms

4-aminoacetanilide, p-amino acetanilide

Depositor-Supplied Synonyms

4′-Aminoacetanilide, N-(4-Aminophenyl)acetamide, 122-80-5, p-Aminoacetanilide, 4-AMINOACETANILIDE, 4-Acetamidoaniline, Acetparamin, p-Amino acetanilide, p-Acetamidoaniline, Acetanilide, 4′-amino-, Fourrine A, p-Acetoaminoaniline, Fourrine 88, 4′-Aminoacetanilid, Acetamide, N-(4-aminophenyl)-, N-Acetyl-p-phenylenediamine, p-(Acetylamino)aniline, 4-(Acetylamino)aniline, Acetyl-p-phenylenediamine, 1-Amino-4-(acetylamino)benzene, C.I. Oxidation Base 19, N-(p-Aminophenyl)acetamide, N-Acetyl-p-fenylendiamin, p-Acetaminoaniline, 4-Acetoamidoaniline, C.I. 76005, NSC 2135, UNII-IH5OX0I3Z9, 4′-Aminoacetanilid [Czech], N1-(4-aminophenyl)acetamide, N-(4-Aminophenyl)-acetamide, CCRIS 2879, CHMBIJAOCISYEW-UHFFFAOYSA-N, N-Acetyl-p-fenylendiamin [Czech], EINECS 204-576-6, MFCD00007853, BRN 0742888, AI3-00069, Paracetamin, 4-Acetaminoaniline, p-acetamino aniline, p-Acetylaminoaniline, ACMC-209amq, AC1Q1KUZ, DSSTox_CID_4455, WLN: ZR DMV1, AC1L1L6V, AC1Q53DF, DSSTox_RID_77404, IH5OX0I3Z9, DSSTox_GSID_24455, Oprea1_124717, SCHEMBL92049, MLS002152920, N-Acetyl-1,4-benzenediamine, acetamide,n-(4-aminophenyl)-, N-(4-amino-phenyl)-acetamide, N-Acetyl-1,4-phenylenediamine, 100528_ALDRICH, 4-N-acetyl-1,4-diaminobenzene, CHEMBL1318876, DTXSID7024455, CTK3J0370, NSC2135, BB_SC-7000, HMS1760L01, HMS3039E03, ZINC152946, NSC-2135, Tox21_200754, ANW-18048, BBL008068, LS-671, SBB028292, STK299393, ZINC00152946, AKOS000108321, MCULE-8040281733, RP01666, TRA-0183651, NCGC00091382-01, NCGC00091382-02, NCGC00258308-01, AJ-12851, AK101063, AN-22891, CAS-122-80-5, I324, OR011109, OR113179, SC-16363, SMR001224520, ZB005292, KB-204412, KB-258188, KB-301437, ST2407380, TR-003636, 4CH-018623, A0106, BB 0216502, FT-0085039, FT-0617543, ST45028084, T6901, 4-13-00-00137 (Beilstein Handbook Reference), I01-0481, W-109456, F0020-1819, T0518-0594, InChI=1/C8H10N2O/c1-6(11)10-8-4-2-7(9)3-5-8/h2-5H,9H2,1H3,(H,10,11

Removed Synonyms

C8H10N2O, MolPort-000-141-720, CID31230, RTR-003636, 4 inverted exclamation mark -aminoacetanilid, 4 inverted exclamation mark -amino-acetanilid

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