HCID 19700990, compound → HCID 19700994, compound

Participants

Reaction Steps

A solution of 4-(4-acetylaminophenyl)-1,2-dihydro-2-(N,N-dimethylcarbamoyl)-1-methyl-6,7-methylendioxyphthalazine (97 mg, 0.25 mmole) in 1N sodium hydroxide (3 mL) and methanol (7 mL) was heated to reflux for 72 hours, cooled to ambient temperature, diluted with EtOAc (25 mL) and water (25 mL). The aqueous layer was washed with EtOAc and the combined organic layers were dried (MgSO4) and evaporated. The residue was chromatographed on silica gel with 25% hexanes/EtOAc to leave a light yellow foamy solid (63 mg, 72%). 200 MHz 1H NMR (CDCl3); δ7.45 (d, 2H, J=8.6 Hz, ArH2 '), 6.84 (s, 1H, ArH), 6.76 (d, 2H, J=8.6 Hz, ArH), 6.71 (s, 1H, ArH), 6.01 (d, 2H, J=2.9 Hz, OCH2O), 5.25 (q, 1H, J=7.1 Hz, CHCH3), 3.95 (brs, 2H, NH2), 3.07 (s, 6H, N(CH3)2), 1.33 (d, 3H, J=7.1 Hz, CHCH3): FTIR (PTFE film); 3456 cm-1, 3343, 3220, 1631, 1605, 1482, 1379, 1251, 1036.

Provenance & Evidence