propyl formate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The product from Example 19 (100 mg) was suspended in propyl form ate (10 ml) and ethanol (1.5 ml). This mixture was boiled under reflux and after 2 minutes triethylamine (0.5 ml) was added. The mixture was boiled under reflux for 4 hours and then cooled and diluted with dichloromethane (50 ml). The mixture was washed with water, then dried, filtered and evaporated to give a residue which was triturated with ether and dichloromethane to give N-{[4-(4,5-dihydro-1H-benzo[g]-indazol-3-yl)-2-pyridyl]methyl}formamide. was added under reflux for 4 hours cooled The mixture was washed with water dried filtered evaporated to give a residue which was triturated with ether and dichloromethane

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: n-Propyl formate (264 g.) and granular sodium cyanide (150 g.) were added successively to a stirred suspension of p-hydroxybenzyl alcohol (8310 g.) in N,N-dimethylformamide (148 g.) and the mixture was heated at 67°-68° C. for 1 hour, cooled to 40° C. and poured into water (588 ml.). The mixture was cooled to 20°-25° C., the pH of the mixture was adjusted from 9.5 to 4.0 with 98% formic acid (270 ml.), and the mixture was extracted three times with isobutyl methyl ketone (677 ml, 196 ml. and 196 ml. successively). Each extract was washed twice with water (196 ml. each time) and the combined extracts were dried by azeotropic distillation under reduced pressure at 60°-70° C. There was thus obtained p-hydroxybenzyl cyanide (319 g., 96% yield). the mixture was heated at 67°-68° C. for 1 hour The mixture was cooled to 20°-25° C. the mixture was extracted three times with isobutyl methyl ketone (677 ml, 196 ml Each extract was washed twice with water (196 ml each time) and the combined extracts were dried by azeotropic distillation under reduced pressure at 60°-70° C

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The product from Example 19 (100 mg) was suspended in propyl form ate (10 ml) and ethanol (1.5 ml). This mixture was boiled under reflux and after 2 minutes triethylamine (0.5 ml) was added. The mixture was boiled under reflux for 4 hours and then cooled and diluted with dichloromethane (50 ml). The mixture was washed with water, then dried, filtered and evaporated to give a residue which was triturated with ether and dichloromethane to give N-{[4-(4,5-dihydro-1H-benzo[g]-indazol-3-yl)-2-pyridyl]methyl}formamide. was added under reflux for 4 hours cooled The mixture was washed with water dried filtered evaporated to give a residue which was triturated with ether and dichloromethane