Hydrochloric Acid → HCID 178463014, compound

Participants

Reaction Steps

1-Ethyl-7-methoxy-N-(phenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine (4 g, 0.012 mol) in DMF (70 ml) is treated with 60% NaH (2.4 g, 0.06 mol), followed by butane thiol (5.4 g, 0.06 mol). The reaction mixture is refluxed overnight and then is poured into ice water. The mixture is acidified with 2N HCl and then is extracted with ethyl acetate (2×500 ml). The aqueous layer is treated with solid NaHCO3 to adjust the pH to about 8, then the mixture is extracted with ethyl acetate (2×500 ml). The ethyl acetate layers are combined, washed with water, filtered and evaporated. The solid residue is recrystallized from ethyl acetate (2×) to afford 1.44 g of 1-ethyl-7-hydroxy-N-(phenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine, m.p. 252°-254° C.

Provenance & Evidence