Methylhydrazine → HCID 87304854, compound

Participants

Reaction Conditions

Reaction Steps

Methyl hydrazine (41.25 mg, 0.8968 mmoles) was added to ethanolic solution of 6-(pyridin-3-yl)imidazo[1,2-a]pyridine-3-carbaldehyde (100 mg, 0.4484 mmoles) at RT. The reaction mixture was heated at 85° C. for 1.5 hours. The solvent was then evaporated. The residue was dissolved in ethanol (5 ml), followed by addition of benzyl isocyanate (140.58 mg, 0.6726 mmoles). The reaction mixture was refluxed for 2 hours, then the solvent was evaporated. Water was poured into the residue and the aqueous solution was extracted with chloroform. Organic layer was separated, washed with water and brine and dried over sodium sulfate. The crude product was purified by column chromatography (100-200 mesh size silica gel, 1.5% methanol in chloroform). Yield: 41%; 1HNMR (DMSO-d6; 300 MHz): δ 9.48 (s, 1H), 9.05 (s, 1H), 8.58 (s, 1H), 8.21 (m, 3H), 7.98 (s, 1H), 7.80 (s, 2H), 7.29 (m, 6H), 4.39 (d, 2H, J=4.2 Hz), 3.35 (s, 3H); MS: m/z 384 (M+1)+.

Provenance & Evidence