1-Chloroethyl chloroformate → HCID 14822508, compound

Participants

Reaction Steps

3-Bromo-7-methoxy-1-(2-methylaminoethyl)-1H-pyrazolo[3,4-b]quinoline was prepared by demethylation of 3-bromo-1-[2-(dimethylamino)ethyl]-7-methoxy-1H-pyrazolo[3,4-b]quinoline (Example 37) by the method of J. Org. Chem. 49, 2081 (1984), as follows: to a mixture of 15 g of the compound of Example 37 and 150 ml methylene dichloride at 0° C. was added dropwise a solution of 6.7 g α-chloroethyl chloroformate in 30 ml methylene dichloride. The reaction mixture was heated at reflux for one hour and then concentrated to remove solvent. The residue in 300 ml methanol was heated at reflux for one hour. The methanol was removed, ice-water and concentrated ammonium hydroxide added to the residue, and the product collected and recrystallized from ethyl acetate to give 7.12 g 3-bromo-7-methoxy-1-(2-methylaminoethyl)-1H-pyrazolo[3,4-b]quinoline, light yellow powder, m.p. 100°-101° C.

Provenance & Evidence