O-ethylhydroxylamine hydrochloride → HCID 136401233, compound

Participants

Reaction Steps

A solution of 1.3 g (3.7 mmol) of 2-propionyl-3-hydroxy-5-(N-(2-propenyl)-3-oxo-(2H)-1,4-benzoxazin-6-yl)cyclohex-2-en-1-one in 20 mL of methyl sulfoxide was treated with 0.43 g (4.5 mmol) of ethoxyamine hydrochloride and 0.36 g (4.4 mmol) of anhydrous sodium acetate. The resulting mixture was stirred at ambient temperature under a nitrogen atmosphere for 6 hours. The reaction mixture was diluted with 200 mL of water and extracted thrice with 20 mL portions of diethylether. The extracts were combined, washed with water, then aqueous sodium chloride, dried over MgSO4 and filtered. Evaporation off of the solvent gave the crude product as a yellow oil which solidified upon standing. The resulting glassy solid was dissolved in a warm 1:1 ether-hexane solution. On cooling, the compound oiled out of the solution and again solidified and was isolated by filtration as a light tan solid. The product was recovered in a yield of 1.1 g (75 percent of theoretical) and melted at 79°-83° C.; 1H NMR(CDCl3): d1.12 (t, J=7 Hz, 3H,--CCH2CH3), 1.32 (t, J=7 Hz, 3H,--OCH2CH3), 2.55-3.55 (m, 7H), 4.16 (q, J=7 Hz, 2H,--OCH2CH3), 4.50-4.70 (m including s at 4.60 for OCH2C=O, 4H, --N--CH2), 5.10-5.42 (m, 2H,--OCH=CH3), 4.70 (s, 2H, --OCH2C=O), 4.88 (s, 2H, --NCH2CN), 6.92-7.20 (m, 3H, aromatic H's), 15.10 (broad s, 1H, enol H); (Compound 5).

Provenance & Evidence