Sodium Hydroxide → HCID 20287803, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 1-oxo-3-thioxo-1H-benz[de]isoquinoline-2(3H)-acetic acid ethyl ester (34.35 g, 0.115 mole, described in Example 6) in methanol (200 ml) and aqueous 4 N sodium hydroxide (43 ml, 0.1721 mole) was stirred at 20° C. for 18 hr. The solvent was removed and the residue suspended in water (1 liter). The aqueous suspension was extracted with ethyl acetate (2×1 liter) to remove unreacted ethyl ester. The aqueous phase was rendered acidic with 2 N hydrochloric acid. The resulting precipitate was collected. Recrystallization of the precipitate from methanol gave 22.5 g of the title compound, mp 265° C. (dec.); UV (MeOH) 244, 251, 333, 344, 390 nm, ε=20,210, 19,150, 8,640, 8,225, 13,995, respectively; IR (nujol) 2900, 1720 and 1683 cm-1 ; NMR (DMSO-d6) δ5.33 (s, 2H), 7.3-8.93 (m, 6H); Anal. Calc'd.: C, 61.98%; H, 3.34%; N, 5.16%; Found: C, 62.07%; H, 3.42%, N, 5.00%.

Provenance & Evidence