Trimethyl orthoformate → (4E)-6-t-butyl-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

Participants

Reaction Conditions

Reaction Steps

An amount 200 mg (0.92 mmol) of 6-tert-butylisoquinoline-1,3(2H,4H)-dione is dissolved in acetic acid 1.0 mL followed by addition of trimethyl orthoformate (25 uL, 2.3 mmol). After, the mixture is heated at 90° C. for 1 h, and cooled to room temperature. The yellow solution evaporated to dryness. Small amounts of anhydrous ether is added and hexane. The yellow solid is collected with hexane to give 188 mg (79% yield) MS (ESI) m/z 260.2 (M+1). 1H NMR (300 MHz, DMSO-d6) 1.346 (S, 9H), 4.178 (S, 3H), 7.472-7.505 (dd, J=1.8 Hz, J=1.8 Hz 1H), 8.007 (d, J=8.52 Hz 2H), 8.31 (d, J=1.71 Hz 1H).

Provenance & Evidence