Homophthalic anhydride → 1(2H)-Isoquinolinone, 3-butyl-

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Reaction Steps

To a solution of 4 g (24 mmol) of homophthalic anhydride in 12 ml of dry pyridine in a 250 L 3 neck flask fitted with a reflux condenser and addition funnel at 0° C. was added 5.4 g (45 mmol) of valeryl chloride in 16 ml of dry chloroform over 45 minutes. The reaction mixture was stirred for a further 1 hour and then was treated with 100 ml of conc. ammonium hydroxide dropwise. The mixture was refluxed for 2 hours and then allowed to stand overnight at room temperature. The two phases were separated and the organic phase was washed with water (1×20 ml). The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The residue was recrystallized from hot MeOH/water to give a pale purple solid.

Provenance & Evidence