Sodium Hydroxide → HCID 178503326, compound

Participants

Reaction Steps

5-Benzyl-7-(methylthio)-1,3,4,5-tetrahydro-1,2,5,6,8-pentaazaacenaphthylene-3-carboxlic acid ethyl ester (3.0 g, 8.1 mmol) and ethanol (55 ml) were placed in a round-bottomed flask. To the sirring mixture was slowly added sodium hydroxide (10% w/w in ethanol, 30 mL, 75 mmol) and allowed to stir at room temperature overnight. The reaction was quenched by addition of citric acid (10% w/v in water, 20 mL) until pH 8. The basic solution was washed with EtOAc (2×100 mL) and then acidified to pH 3 with citric acid (10% w/v in water, 50 mL). The resulting acidic solution was extracted with EtOAc (3×100 mL) and dichloromethane (1×50 mL). The organic washes were combined, dried over MgSO4, and concentrated under reduced pressure to yield a yellow solid (2.25 g, 6.6 mmol). 1H-NMR (DMSO-d6): 13.1 (bs, 1H), 7.40-7.22 (m, 5H), 4.36 (dd, J=5.1, 13.2 Hz, 3H), 4.22 (t, J=5.2 Hz, 2H), 3.86-3.76 (m, 3H), 3.17 (d, J=5.2 Hz, 1H). LC: Rt=1.19 min. MS 342.42 [M+H]

Provenance & Evidence