Methanol → HCID 19066090, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 737 mg (2.09 mmol) of the title compound of Example 1, 70 ml of methanol, and 30 ml of water chilled to 0° C. in an ice bath was added 210 mg (5.22 mmol, 2.5 equivalents) of sodium hydroxide. After the sodium hydroxide had dissolved, the ice bath was removed and the mixture was allowed to stir at room temperature for 3 hours. The solvent was removed by rotary evaporation and the residue was diluted with water, chilled to 0° C. in an ice bath, and acidified with aqueous 6N HCl solution until precipitation had ceased. The precipitate was collected by filtration (washed with cold water) and was dried under vacuum to yield 554 mg (85%) of the title compound, mp 233°-235° C. 1H NMR (DMSO-d6): δ 2.29 (3H, s), 3.85 (2H, s), 7.38 (1H, dd, J=8, 5), 8.33 (1H, d, J=8), 8.63 (1H, d, J=5). FAB MS (m/e): 311 (M+ +1), 265, 233, 119 (base).

Provenance & Evidence