Synthesis of N-methyl-4-nitrosoaniline

Preparation of N-methyl-4-nitrosoaniline

10 g methylaniline dissolved in 15 ml conc. hydrochloric acid and 40 g ice are treated with 7 g sodium nitrite in 25 ml water. N-Nitroso-N-methylaniline separates as a yellow oil, which solidifies on cooling (m.p. 12°-15° C). 2 g N-Nitroso-N-methylaniline are dissolved in 4 g ether and 8 g absolute alcohol which have been saturated with hydrochloric acid gas then added. After a time needles separate out which are filtered and washed with a mixture of alcohol and ether. Yield almost theoretical, m.p. 118° C.

Systematic organic chemistry, by W. M. Cumming, 285-286, 1937.

IUPAC Name

N-methyl-4-nitrosoaniline

InChI

InChI=1S/C7H8N2O/c1-8-6-2-4-7(9-10)5-3-6/h2-5,8H,1H3

InChI Key

ZPHCTSKOFFWBHL-UHFFFAOYSA-N

Canonical SMILES

CNC1=CC=C(C=C1)N=O

MeSH Synonyms

4-nitroso-N-methylaniline, 4-nitrosomethylaniline, p-nitrosomethylaniline, para-nitrosomethylaniline

Depositor-Supplied Synonyms

N-Methyl-4-nitrosoaniline, N-Methyl-p-nitrosoaniline, 4-Nitroso-N-methylaniline, N-Methyl-4-nitrosobenzenamine, p-Nitrosomethylaniline [French], 10595-51-4, Benzenamine, N-methyl-4-nitroso-, ANILINE, N-METHYL-p-NITROSO-, NSC 66522, NSC677514, BRN 2077886, NSC66522, p-Nitrosomethylaniline, AC1Q40XK, N-methyl-4-nitroso-aniline, SCHEMBL537959, Benzenamine,N-methyl-4-nitroso-, CTK4A4237, MolPort-001-783-362, ZPHCTSKOFFWBHL-UHFFFAOYSA-N, AC1L1930, N-Methyl-N-(4-nitrosophenyl)amine, ZINC4558915, NSC-66522, AKOS006272317, MCULE-8008771326, NSC-677514, Benzenamine, N-methyl-4-nitroso- (9CI), LS-19895, OR038275, KB-259011, 3-07-00-03370 (Beilstein Handbook Reference)

Removed Synonyms

CID25417

Share This

Leave a Reply

Your email address will not be published.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