Trifluoroacetic acid → 2-(Trifluoromethyl)-decahydroquinoline

HRID 1647272Notes

Reaction equation

HRID 1647272 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.C(O)(C(F)(F)F)=O>O1CCCC1.[Ru]>[F:14][C:2]([F:1])([F:13])[CH:3]1[CH2:12][CH2:11][CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[NH:4]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 27778052-(Trifluoromethyl)quinoline

Product 1

HCID 199732332-(Trifluoromethyl)-decahydroquinoline

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

15 g (0.076 mol) of 2-(Trifluoromethyl)quinoline [prepared from quinoline-2-carboxylic acid according to M. S. Raasch, J. Org. Chem. 27, 1406 (1962)] were hydrogenated in 100 ml of tetrahydrofuran on 2.5 g of ruthenium on alumina (about 10% RU content) at 180° C. for 8 h at an H2 pressure of 80-100 bar in a 0.3 1 V4A autoclave. After filtration, the THF was stripped off and the crude product was fractionated in a water pump vacuum by means of a microdistillation apparatus. B.p.16 (main fraction): 88° C. Yield: 12.5 g (0.061 mol) (80% of theory) The product was obtained as a diastereomer mixture. 19F--NMR: δ=+0.65 ppm(d, JH-F =7.1 Hz)(according to integral about 88%) 19F--NMR: δ=+0.90 ppm(d, JH-F =7.1 Hz)(according to integral about 12%) (against external CF3COOH).

Workup

  1. filtrationAfter filtration
  2. custom88° C
  3. customYield: 12.5 g (0.061 mol) (80% of theory) The product was obtained as a diastereomer mixture

Sources & evidence

ORD record
ord-e94674a8214a40bf8c24685376fc9b55
Source dataset
uspto-grants-1995_07
Patent number
US05430151

Reaction notes

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