Hydrochloric Acid → HCID 58288427, compound

Participants

Reaction Steps

A solution of 1.58 g (5.61 mmol) of a mixture of tert-butyl (2E)-3-(3-amino-4-chloro-2-methylphenyl)-2-methylacrylate and tert-butyl 2-(3-amino-4-chloro-2-methylbenzyl)acrylate (Example 135A) in 5.0 ml of methanol was added to 354 mg (14.6 mmol) of magnesium turnings and a few grains of iodine. The mixture was stirred at RT (initially with cooling) overnight. 50 ml of 1 N hydrochloric acid were then added with ice-cooling. By addition of 10% strength aqueous sodium hydroxide solution, the pH of the mixture was then adjusted to about 10. The mixture was extracted three times with ethyl acetate. The combined organic phases were dried over magnesium sulphate and concentrated under reduced pressure. The crude product gave, after chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 50:1 to 40:1), 962 mg of the target product (60.5% of theory).

Provenance & Evidence