Ethyl 4,4,4-trifluoroacetoacetate → 2-Hydroxyquinoline

Participants

Reaction Steps

This compound was prepared in a manner similar to that described for Compound 102 (EXAMPLE 2) with 7-amino-1,2-dihydro-2,2,4,8-tetramethylquinoline (100 mg, 0.49 mmol) and ethyl 4,4,4-trifluoroacetoacetate (107 mL, 0.73 mmol, 1.5 equiv), affording 75 mg (47%) of the desired 2-quinolone as a fluorescent-yellow solid. Data for 1,2-dihydro-2,2,4,10-tetramethyl-6-trifluoromethyl-8-pyridono[5,6-f]quinoline: 1H NMR (400 MHz, CDCl3) 9.23 (br s, 1H, CONH), 7.37 (s, 1H, 5-H), 6.67 (s, 1H, 7-H), 5.45 (s, 1H, 3-H), 4.14 [br s, 1H, (CH3)2CNH], 2.12 (s, 3H, 10-CH3), 2.04 (d, 3H, J=1.1 Hz, 4-CH3), 1.37 [s, 6H, 2-(CH3)2 ].

Provenance & Evidence