Hydrochloric Acid → HCID 69951655, compound

Participants

Reaction Conditions

Reaction Steps

Potassium t-Butoxide 1M in THF (80 mL) was added slowly to a solution of p-hydroxyphenyl glycine benzylimine (10.7 g, 36.2 mmol) in THF (250 mL) cooled to 0° C. under a nitrogen atmosphere. The reaction was stirred for 1 h, then allyl bromide (4.38 g, 36.2 mmol) was added slowly giving a slurry. The reaction was stirred for an additional hour then 4-chloromethyl 2-methyl quinoline (6.93 g, 36.1 mmol) and tetrabutyl ammonium iodide (20 mol %) was added. The reaction mixture was allowed to warm to 40° C. for 2 h then allowed to stir at RT overnight. 1N HCl (80 mL) and water (100 mL) were added to the reaction, stirred for 1 h and washed with ethyl ether (2×100 mL). The organic layer was back washed with 1N HCl (50 mL). The combined aqueous layers were neutralized with sodium hydroxide (50%) and extracted with ethyl acetate (3×150 mL). The combined ethyl acetate layers were dried over magnesium sulfate and concentrated to give a dark oil. The oil was taken up in 125 mL ethanol and methanesulfonic acid (2 eq) was added. This was stirred at RT to give a precipitate. The solids were collected and dried to give 2-allyl p-hydroxyphenyl glycine (12.1 g, 70%) as a yellow powder MS (M+H)+=391.

Provenance & Evidence