4-fluoro-2-methyl-N-(2,2,2-trifluoroethyl)aniline

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 66.1 g of 4-fluoro-2-methyl-N-(2,2,2-trifluoroethyl)aniline and 75.0 g of diethyl ethoxymethylenemalonate was heated at 160° for 20 hours. Eight hundred grams of polyphosphoric acid (ca. 400 ml) was added and the resulting mixture heated at 105°-115° for 20 minutes. The hot reaction mass was poured onto 1 kg of cracked ice to hydrolyze the polyphosphoric acid; the resulting solid was filtered and recrystallized from acetonitrile to yield 45.2 g of 6-fluoro-1,4-dihydro-8-methyl-4-oxo-1-(2,2,2-trifluoroethyl)-3-quinolinecarboxylic acid, ethyl ester, m.p. 154°-158°. was heated at 160° for 20 hours the resulting mixture heated at 105°-115° for 20 minutes the resulting solid was filtered recrystallized from acetonitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 66.1 g of 4-fluoro-2-methyl-N-(2,2,2-trifluoroethyl)aniline and 75.0 g of diethyl ethoxymethylenemalonate was heated at 160° for 20 hours. Eight hundred grams of polyphosphoric acid (ca. 400 ml) was added and the resulting mixture heated at 105°-115° for 20 minutes. The hot reaction mass was poured onto 1 kg of cracked ice to hydrolyze the polyphosphoric acid; the resulting solid was filtered and recrystallized from acetonitrile to yield 45.2 g of 6-fluoro-1,4-dihydro-8-methyl-4-oxo-1-(2,2,2-trifluoroethyl)-3-quinolinecarboxylic acid, ethyl ester, m.p. 154°-158°. was heated at 160° for 20 hours the resulting mixture heated at 105°-115° for 20 minutes the resulting solid was filtered recrystallized from acetonitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 66.1 g of 4-fluoro-2-methyl-N-(2,2,2-trifluoroethyl)aniline and 75.0 g of diethyl ethoxymethylenemalonate was heated at 160° for 20 hours. Eight hundred grams of polyphosphoric acid (ca. 400 ml) was added and the resulting mixture heated at 105°-115° for 20 minutes. The hot reaction mass was poured onto 1 kg of cracked ice to hydrolyze the polyphosphoric acid; the resulting solid was filtered and recrystallized from acetonitrile to yield 45.2 g of 6-fluoro-1,4-dihydro-8-methyl-4-oxo-1-(2,2,2-trifluoroethyl)-3-quinolinecarboxylic acid, ethyl ester, m.p. 154°-158°. was heated at 160° for 20 hours the resulting mixture heated at 105°-115° for 20 minutes the resulting solid was filtered recrystallized from acetonitrile