HCID 12674740, compound → HCID 13533224, compound

Participants

Reaction Conditions

Reaction Steps

50 g of α-bromobutyric acid bromide (V), 50 g of anhydrous aluminum chloride and 400 ml of carbon disulfide were added to 20 g of 8-hydroxycarbostyril (VI). The resulting mixture was heated at a temperature of 50° C for 13 hours and the carbon disulfide layer was removed by decantation. Crushed ice was added to the residue, and the precipitated crystals were filtered, washed with water and recrystallized from methanol to obtain 27 g of 5-(α-bromobutyryl)-8-hydroxycarbostyril (IV) having a melting point of 218°-219° C (with coloring and decomposition). To 5 g of the thus obtained 5-(α-bromobutyryl)-8-hydroxycarbostyril (IV) was added 100 ml of iso-propylamine (III), and the mixture was heated at a temperature of 50° C for 4 hours followed by concentration to dryness. Crystals which formed upon addition of water were filtered, washed with water and then recrystallized from methanol to obtain 4.6 g ofa methanol solvate of 5-(α-iso-propylaminobutyryl)-8-hydroxycarbostyril (II) having a melting point of 136°-137° C (with foaming and decomposition).

Provenance & Evidence