HCID 10012728, compound → 2-(Isoxazol-5-yl)aniline

Participants

Reaction Conditions

Reaction Steps

5-(2-nitrophenyl)isoxazole (850 mg, 4.5 mmol), prepared as in Example 101, was added portionwise to a suspension of stannous chloride dihydrate (3.3 g, 14.6 mmol) in concentrated hydrochloric acid (8.3 mL). The reaction was heated to 105° C. four 1 hour. The reaction was cooled to 10° C. and filtered, and the solid was added to water (10 mL). The solution was adjusted to pH 10 with 10N sodium hydroxide, and extracted with methylene chloride. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo to give 5-(2-aminophenyl)isoxazole (220 mg), which was coupled with CMI under conditions described in the general procedure for CMI coupling to give the hydrochloric acid salt of N-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2-(5-isoxazolyl)aniline.

Provenance & Evidence