Sodium Carbonate → 4-(1-Acetyl-1,2,3,4-tetrahydroquinolin-6-yl)-3-methylbenzoic acid

Participants

Reaction Steps

4-Borono-3-methylbenzoic acid (D29) (220 mg, 1.2 mmol), 1-acetyl-1,2,3,4-tetrahydro-6-trifluoromethanesulphonyloxyquinoline (D41, 410 mg, 1.25 mmol), lithium chloride (150 mg, 3.6 mmol) and sodium carbonate (505 mg, 4.7 mmol) were dissolved in a mixture of water (10 ml) and dimethoxyethane (10 ml). The suspension was degassed with argon for 15 mins and then treated with tetrakis (triphenylphosphine)palladium (O) (68 mg). The reaction mixture was heated at reflux for 28 hrs, then concentrated in vacuo. The residue was treated with 10% aqueous Na2CO3 solution and washed with ethyl acetate. The aqueous layer was acidified with 5M HCl and the resultant precipitate was filtered off and dried to afford the title compound as a light brown solid (386 mg, 100%).

Provenance & Evidence