Synthesis of 3-Cyano-4-methylpyridine

Preparation of 3-cyano-4-methylpyridine

Alternative Names: 4-methylnicotinonitrile; 3-Cyano-4-picoline; 4-methylpyridine-3-carbonitrile; 4-methyl-nicotinonitrile;

A mixture of 1 equiv. of 4-methylpyridine-3-carbaldehyde and 1.1 equiv. of hydroxylamine hydrochloride are mixed with the dimethylsulfoxide until the homogeneous mixture is obtained (3-5 volumes) and the obtained mixture is stirred at 90° C for 1-2 hours. The reaction is monitored by TLC (ethyl acetate:hexane 5:95) and when is completed the mixture is cooled and poured in water,  the reaction product is extracted with ether, dried and the ether is removed by evaporation affording 96% of the 3-cyano-4-methylpyridine.

J. K. Augustine, et al. Synlett, 2223-2227, (2011) (supporting information)

IUPAC Name

4-methylpyridine-3-carbonitrile

InChI

InChI=1S/C7H6N2/c1-6-2-3-9-5-7(6)4-8/h2-3,5H,1H3

InChI Key

XLAPHZHNODDMDD-UHFFFAOYSA-N

Canonical SMILES

CC1=C(C=NC=C1)C#N

MeSH Synonyms

4-methyl-3-cyanopyridine

Depositor-Supplied Synonyms

3-Cyano-4-methylpyridine, 4-methylnicotinonitrile, 5444-01-9, 3-Cyano-4-picoline, 4-methylpyridine-3-carbonitrile, 4-methyl-nicotinonitrile, AC-907/25004626, NSC19882, PubChem6623, PubChem18426, AC1L5FRD, AC1Q2RAN, 4-methyl-3-cyanopyridine, ACMC-2097ho, KSC497O5F, SCHEMBL211613, CTK3J7752, MolPort-001-768-232, XLAPHZHNODDMDD-UHFFFAOYSA-N, 3-Pyridinecarbonitrile, 4-methyl-, ACN-S004446, ACT01570, ANW-13978, AR-1G3748, CC-040, NSC-19882, SBB055519, ZINC00330972, AKOS005146414, 4-METHYL-3-PYRIDINECARBONITRILE, AC-3313, DS-0655, LS20001, PB24636, PS-4837, RL04031, RP09528, RTR-037046, AJ-19372, AK-28504, AN-13130, BR-28504, C194, CJ-02767, EN002250, HC150241, KB-31413, N318, SY004551, AB1004272, DB-005293, ST2418491, TR-037046, 3-Cyano-4-picoline; 4-Methylnicotinonitrile, 4CH-015549, AM20061304, FT-0081660, FT-0601208, FT-0677158, A-5695, I02-0273

Removed Synonyms

CID227806, 10270-28-7

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