Synthesis of 3′-aminoacetophenone

Preparation of 3′-aminoacetophenone

Preparation of 3'-aminoacetophenone

Preparation of 3′-aminoacetophenone

A solution of 295 g of 3-nitroacetophenone (Org. Syntheses Coll. Vol. 2, 434 (1943)) in 1.1 liter of absolute ethanol is shaken with 1.5 tablespoons of Raney nickel catalyst at 50° under an initial hydrogen pressure of 1950 lb. After uptake of hydrogen has ceased, the solvent is evaporated and the residue triturated with 400 ml of a mixture of cold water and excess concentrated hydrochloric acid. The undissolved portion after filtration is treated again with hydrochloric acid. The combined insoluble portions from four reduction batches are washed with water until free from acid and dried (170 g) and subjected to reduction as before. The combined hydrochloric acid solutions are treated with solid sodium carbonate with stirring until the solution is alkaline, and the precipitated 3′-aminoacetophenone is removed by filtration, washed with cold water, and dried, giving 687 g (71%) of product melting at 92-94°.

J. Am. Chem. Soc., 68, 1089 (1946)

IUPAC Name

1-(3-aminophenyl)ethanone

InChI

InChI=1S/C8H9NO/c1-6(10)7-3-2-4-8(9)5-7/h2-5H,9H2,1H3

InChI Key

CKQHAYFOPRIUOM-UHFFFAOYSA-N

Canonical SMILES

CC(=O)C1=CC(=CC=C1)N

MeSH Synonyms

3′-aminoacetophenone, 3-aminoacetophenone, m-aminoacetophenone, meta-aminoacetophenone

Depositor-Supplied Synonyms

3′-Aminoacetophenone, 1-(3-Aminophenyl)ethanone, 99-03-6, m-Aminoacetophenone, 3-Acetylaniline, 3-AMINOACETOPHENONE, m-Acetylaniline, Ethanone, 1-(3-aminophenyl)-, m-Aminoacetylbenzene, Acetophenone, 3′-amino-, Acetophenone, m-amino-, 3-Aminoacetofenon, beta-Aminoacetophenone, 1-(3-aminophenyl)ethan-1-one, .beta.-Aminoacetophenone, NSC 7637, 3-Aminoacetofenon [Czech], 1-(3-amino-phenyl)-ethanone, CKQHAYFOPRIUOM-UHFFFAOYSA-N, EINECS 202-722-3, SBB058713, BRN 0386009, 1-acetyl-3-aminobenzene, AI3-14674, 3-Acetylphenylamine, 3-acetyl-phenylamine, 3-amino acetophenone, PubChem6391, 3′-amino acetophenone, 3′-Amino-acetophenone, AC1L1OPS, AC1Q1JVZ, AC1Q5CBV, AC1Q1JM2, WLN: ZR CV1, ACETOPHENONE,3-AMINO, 1-(3-aminophenyl)-ethanone, KSC490E0J, SCHEMBL330495, 139351_ALDRICH, 06629_FLUKA, 06630_FLUKA, CTK3J0204, NSC7637, MolPort-000-150-919, ZINC157542, ACMC-209792, NSC-7637, STR02986, ANW-13668, AR-1F1625, STL168894, ZINC00157542, AKOS000119494, MCULE-6635867482, RP20207, RTR-038646, TRA0074933, AJ-15055, AK-83273, BR-83273, CJ-01684, HE030094, KB-63886, LS-13358, OR111515, SC-46716, AB1001944, DB-029992, ST2408549, TR-038646, A0249, ST45255306, M-7250, 4-14-00-00096 (Beilstein Handbook Reference), I01-1630, I01-5791, T7105934, W-100056, InChI=1/C8H9NO/c1-6(10)7-3-2-4-8(9)5-7/h2-5H,9H2,1H, 3AO

Removed Synonyms

CID7417, A1465, 2051-04-9

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