HCID 387663, compound → HCID 387662, compound

Participants

Reaction Conditions

Reaction Steps

Sodium acetate (2.86 g, 35 mmol) was added to a stirred solution of 6-oxo derivative (9) (0.45 g, 1.2 mmol) in methanol (55 mL). Hydroxylamine hydrochloride salt (2.2 g, 32 mmol) in water (3 mL) was then added at room temperature. The resulting mixture was stirred at 90° C. for 6 h. Then solvent was removed under reduced pressure, the resulting residue was diluted with water (60 mL), and product was extracted into ethyl acetate (3×120 mL). The combined organic layer was washed with water (70 mL), brine (70 mL), and dried over anhydrous sodium sulfate. The organic layer on evaporation under reduced pressure provided the crude product, which on crystallization from ethyl acetate-hexane mixture gave oxime (12) (0.3 g, 65%): mp 187-191° C.; IR (KBr) 3330, 2960-2860, 1500, 880, 750 cm-1 ; 1H NMR (CDCl3 +DMSO-d6 +D2O) δ 0.77 (s, 3 H), 1.10-2.38 (m, 11 H), 2.67 (s, 2 H), 3.05-3.27 (m, 2 H), 3.72 (t, J=8.5 Hz, 1 H), 4.50 (q, J=8.5 Hz, 2 H), 6.88 (s, 1 H), 7.57 (s, 1 H) 10.20 (s, 1 H). Anal. (C20H24NF3O4) C, H.

Provenance & Evidence