Ethyl 4,4,4-trifluoroacetoacetate → HCID 12378169, compound

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Reaction Steps

This is a representative procedure for making azaquinolones. 7-Amino-1,4-dimethyl-1,2,3,4-tetrahydro-1,8-naphthyridine (0.9 g.) and 1.0 g. of ethyl trifluoroacetoacetate were heated at 145°-165° for 18 hours. The cooled, semisolid mass was slurried with 5 ml. of ether, filtered and washed with more ether, 1.3 g., m.p. 225°-230°, wet 200°. Other data are found in the table. 1H nmr (deuteriochloroform, 100 MHz): δ1.30 (d,3H, CH3CH, J=7 Hz), 1.74 (m, 1H, H7a or H7b), 1.89 (m, H, H7a or H7b), 2.92 (m, 1H, H6), 3.20 (s, 3H, NCH3), 3.49 (t, 2H, H8, H8, J=6 Hz), 6.62 (s, 1H, H3), 7.46 (q, 1H, H5, JH5 --CF3 =~1.5 Hz), 9.40 (broad s, 1H,NH).

Provenance & Evidence