Hydrazine hydrate (1:1) → HCID 19592299, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-chloro-8-(2,6-dichlorobenzoylamino)-3-hydroxymethylquinoline (297 mg) in N-methylpyrrolidone (4 ml) was added hydrazine monohydrate (390 mg), and the mixture was stirred for 3 hours at 90° C. The mixture was diluted with ethyl acetate, washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash chromatography on silica gel and by preparative thin layer chromatography to give 8-(2,6-dichlorobenzoylamino)-4-hydrazino-3-hydroxymethylquinoline (127 mg) and 6-(2,6-dichlorobenzoylamino)-1H-pyrazolo[4,3-c]-quinoline (90 mg). 8-(2,6-Dichlorobenzoylamino)-4-hydrazino-3-hydroxymethylquinoline NMR (DMSO-d6, δ): 4.70 (2H, d, J=6 Hz), 5.19 (2H, s), 5.35 (1H, t, J=6 Hz), 7.39 (1H, dd, J=8, 8 Hz), 7.49-7.63 (3H, m), 8.15 (1H, d, J=8 Hz), 8.28 (1H, s), 8.40 (1H, s), 8.56 (1H, d, J=8 Hz), 10.46 (1H, s) 6-(2,6-Dichlorobenzoylamino)-1H-pyrazolo[4,3-c]quinoline NMR (DMSO-d6, δ): 7.49-7.63 (3H, m), 7.77 (1H, dd, J=8, 8 Hz), 8.20 (1H, d, J=8 Hz), 8.46 (1H, br s), 8.78 (1H, d, J=8 Hz), 9.25 (1H, s), 10.76 (1H, s)

Provenance & Evidence