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

HRID 2209544Notes

Reaction equation

HRID 2209544 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-394232c60221424a9679deeacaea0432
Source dataset
uspto-grants-1995_10
Patent number
US05455253

Reaction notes

Loading…