Water → 4-[2-[4-Methyl-1-oxo-1,2-dihydro-phthalazin-2-yl]ethoxy]benzaldehyde

Participants

Reaction Conditions

Reaction Steps

##STR30## To a stirred suspension of K2CO3 (11.3 g, 82.5 mmol) in dry DMF (50 mL) at 25-30° C. was added a solution of 4-methyl-1(2H)-phthalazinone (6.6 g, 41.25 mmol) (Ref: Chemistry of Heterocyclic Compounds; Condensed Pyridazines including Cinnolines and Phthalazines, edited by R. N. Castle; John Wiley and Sons, 27, (1973) 375-441) in dry DMF (100 mL). The reaction mixture was stirred for 30 min at 25° C. and 4-(2-bromoethoxy)benzaldehyde (9.4 g, 41.25 mmol) was added. The reaction mixture was immersed in a pre-heated oil bath at 70° C. and stirred at 65-70° C. for 24 h. The reaction mixture was cooled to room temperature and water (50 mL) was added. The reaction mixture was extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated. The crude compound was recrystallised from methanol to obtain the title compound (9.7 g, 77%). mp: 90° C.

Provenance & Evidence