Water → HCID 67441733, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-[(pyridin-3-ylmethylene)-amino]-benzoic acid ethyl ester (51 g, 200 mmol) and Ytterbium(III) triflate hydrate (12.4 g, 20 mmol) in dry tetrahydrofuran (200 mL) at 25° C. was added isobutyraldehyde (18.2 mL, 200 mmol) and water (3.6 mL, 200 mmol) dropwise. The reaction mixture was stirred at 25° C. for 16 h. Then the reaction mixture was concentrated in vacuo and the residue was extracted with ethyl acetate (2×200 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 4-hydroxy-3,3-dimethyl-2-pyridin-3-yl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (65.2 g, quant.) as a light yellow oil which was used for next step without further purification: LC/MS m/e calcd for C19H22N2O3 (M+H)+: 327.40, observed: 309.0.

Provenance & Evidence