4-(Trifluoromethyl)aniline → Methyl 4-hydroxy-6-(trifluoromethyl)quinoline-2-carboxylate
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[CH3:12][O:13][C:14]([C:16]#[C:17][C:18](OC)=[O:19])=[O:15]>>[F:11][C:8]([F:9])([F:10])[C:5]1[CH:6]=[C:7]2[C:2](=[CH:3][CH:4]=1)[NH:1][C:16]([C:14]([O:13][CH3:12])=[O:15])=[CH:17][C:18]2=[O:19]Participants
3
Procedure
Using the method described in Example 18a with 4-aminobenzotrifluoride (20 g) and dimethylacetylene dicarboxylate (17.5 g) as reagents gave methyl 6-trifluoromethyl-4-oxo-1,4-dihydroquinoline-2-carboxylate (0.91 g), m.p. 289°-291° C., δ (360 MHz, DMSO-d6) 3.98 (3H, s, CH3), 6.74 (1H, s, 3-H), 8.02 (1H, dd, 7-H), 8.13 (1H, d, 8-H), 8.33 (1H, s, 5-H) and 12.40 (1H, s, NH).
Sources & evidence
- ORD record
- ord-baf8552dcfcd473dbc5d70e8f0b42c33
- Source dataset
- uspto-grants-1993_12
- Patent number
- US05270309
Reaction notes
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