Synthesis of 2-methoxy-5-acetylaniline

Preparation of 2-methoxy-5-acetylaniline (3-amino-4-methoxyacetophenone)

Preparation of 2-methoxy-5-acetylaniline (3-amino-4-methoxyacetophenone)

Preparation of 2-methoxy-5-acetylaniline (3-amino-4-methoxyacetophenone)

A solution of 180 g. of stannous chloride dihydrate in 180 ml. of concentrated hydrochloric acid is cooled to 0°, and 40 g. of 3-nitro-4-methoxyacetophenone is added all at once with stirring. The cooling bath is removed, and when the temperature of the reaction mixture has reached 95° it is cooled to 85° and the cooling bath is removed again. The mixture is stirred and allowed to cool to room temperature, and the precipitated solid is filtered off. The solid is treated with 50 ml. of water and an excess of 40% aqueous sodium hydroxide solution. The precipitated amine is filtered off, washed with water, and recrystallized from alcohol to give 25.7 g. (76%) of 3-amino-4-methoxyacetophenone, m.p. 100-101°.

J. Am. Chem. Soc., 70, 1251 (1948).

IUPAC Name

1-(3-amino-4-methoxyphenyl)ethanone

InChI

InChI=1S/C9H11NO2/c1-6(11)7-3-4-9(12-2)8(10)5-7/h3-5H,10H2,1-2H3

InChI Key

LRUQWUYHWFRXPC-UHFFFAOYSA-N

Canonical SMILES

CC(=O)C1=CC(=C(C=C1)OC)N

Depositor-Supplied Synonyms

2-Methoxy-5-acetylaniline, 1-(3-Amino-4-methoxyphenyl)ethanone, 6318-64-5, Ethanone, 1-(3-amino-4-methoxyphenyl)-, 4-Methoxy-3-aminoacetophenone, 3′-Amino-4′-methoxyacetophenone, LRUQWUYHWFRXPC-UHFFFAOYSA-N, Acetophenone, 3′-amino-4′-methoxy-, SBB018620, 1-acetyl-3-amino-4-methoxybenzene, NSC31675, AC1L5PPB, AC1Q5EEI, 2-methoxy 5-acetyl aniline, 3-Amino-4-methoxyacetophenone, SCHEMBL3124632, CTK5B7993, MolPort-001-788-511, ZINC1663931, AR-1E3112, NSC-31675, STK727278, ZINC01663931, AKOS000296236, 1-(3-amino-4-methoxy-phenyl)ethanone, MCULE-3590854275, 1-(3-amino-4-methoxy-phenyl)-ethanone, 1-(3-Amino-4-methoxyphenyl)ethanone #, AJ-28954, AK124732, OR141670, KB-213606, ST4144254, W-6286

Removed Synonyms

CID233283, 701-47-3

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