HCID 12985697, compound → HCID 12985709, compound

Participants

Reaction Steps

4-[(3-Ethylphenyl)amino]-1-methyl-1H-pyrazole-5-carboxylic acid (EXAMPLE 8 and 9, step 1) was treated according to the procedure of step 2 in EXAMPLE 3 instead of 4-[(3-fluorophenyl)amino]-1-methyl-1H-pyrazole-5-carboxylic acid. The obtained inseparable mixture of 9-chloro-8-ethyl-1-methyl-1H-pyrazolo[4,3-b]quinoline and 9-chloro-6-ethyl-1-methyl-1H-pyrazolo[4,3-b]quinoline (200 mg, 0.81 mmol) in 50% aqueous acetic acid (8 ml) was refluxed for 8 h. After cooling to room temperature, the mixture was concentrated and chromatographed on a column of silica gel with ethyl acetate/hexane (1:2) to afford 75 mg (41%) of 8-ethyl-1-methyl-1,4-dihydro-9H-pyrazolo[4,3-b]quinolin-9-one as a solid and 103 mg (56%) of 6-ethyl-1-methyl-1,4-dihydro-9H-pyrazolo[4,3-b]quinolin-9-one as a solid.

Provenance & Evidence