Water → 2-Trifluoromethyl-4-(3-cyanophenyl)-4, 6,7,8-tetrahydro-5(1H)-quinolone

HRID 54461Notes

Reaction equation

HRID 54461 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]2[C:18]3[C:17](=[O:19])[CH2:16][CH2:15][CH2:14][C:13]=3[NH:12][C:11]([C:20]([F:23])([F:22])[F:21])=[C:10]2C(O)=O)[CH:6]=[CH:7][CH:8]=1)#[N:2].O.C(Cl)Cl.CCOCC.C(OCC)C.CCCCCC>CN1CCCC1=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]2[C:18]3[C:17](=[O:19])[CH2:16][CH2:15][CH2:14][C:13]=3[NH:12][C:11]([C:20]([F:23])([F:21])[F:22])=[CH:10]2)[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 101937582-(Trifluoromethyl)-4-(3-cyanophenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acidHCID 21584099Diethylether hexaneHCID 21881112Ethyl ether methylene chloride

Product 1

HCID 111629272-Trifluoromethyl-4-(3-cyanophenyl)-4, 6,7,8-tetrahydro-5(1H)-quinoloneYield 99%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A stirred solution of (-)-4-(3-cyanophenyl)-2-trifluoromethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid (3.93 g, 10.85 mmol) in N-methylpyrrolidin-2-one (24 mL) was placed in a preheated oil bath at 210° C. for 20 minutes. The cooled reaction mixture was then poured into water (200 mL) and extracted twice with ethyl ether. The combined ether extracts were washed twice with water, dried (MgSO4), filtered and the solvent removed to yield an off-white solid. Chromatography (eluent: methylene chloride/ether 9:1) and trituration with ethyl ether/hexane provided the title compound (3.42 g, 79%) as a white solid mp 187°-189° C. NMR: 1.88-1.91 (m,2H, CH2), 2.21-2.25 (m,2H, CH2), 2.53-2.64 (m,2H, CH2), 4.68(d,1H, J=5.3 Hz, CH), 5.61 (d,1H, J=5.3 Hz, CH), 7.50-7.54 (m,2H, Ar), 7.61-7.66 (m,2H, Ar), 9.42 (s,1H, NH); MS: m/z=319(M+1); [α]D23 =-606.8° (c=0.665 methanol). Analysis for C17H13F3N2O: Calculated: C, 64.14; H, 4.12; N, 8.80; Found: C, 64.07; H, 4.24; N, 8.78.

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted twice with ethyl ether
  3. washThe combined ether extracts were washed twice with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed
  7. customto yield an off-white solid

Sources & evidence

ORD record
ord-d3dae36e4d70465c8f6b72f893e0d140
Source dataset
uspto-grants-1997_04
Patent number
US05622964

Reaction notes

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