Sodium Carbonate → 2-Chloro-6-(trifluoromethyl)quinoline

HRID 1772211Notes

Reaction equation

HRID 1772211 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=O)[CH:7]=[CH:6]2.C([O-])([O-])=O.[Na+].[Na+].O=P(Cl)(Cl)[Cl:24]>>[Cl:24][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([C:2]([F:15])([F:14])[F:1])[CH:4]=2)[N:9]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 337462666-(Trifluoromethyl)quinolin-2(1H)-one

Product 1

HCID 109114112-Chloro-6-(trifluoromethyl)quinolineYield 87%

Conditions

Temperature
110 °C

Procedure

6-(trifluoromethyl)-1,2-dihydroquinolin-2-one (1.0 g, 4.7 mmol) was dissolved in POCl3 (15 ml) and stirred for 2 h at 110° C. (oil bath). The resulting mixture was dissolved in ice-water (100 ml) and adjusted pH to 8 with aqueous Na2CO3 solution (3N). The crude product was then extracted with dichloromethane (3×80 ml) and the organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum to afford 2-chloro-6-(trifluoromethyl)quinoline as a dark red solid (944 mg, 87%). (ES, m/z): [M+H]+ 232. 1H NMR (300 MHz, DMSO): δ 8.59-8.66 (m, 2H), 8.01-8.17 (m, 2H), 7.75 (d, J=8.7 Hz, 1H).

Workup

  1. extractionThe crude product was then extracted with dichloromethane (3×80 ml)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ea68fcc0474e43a48e9a3a954886c760
Source dataset
uspto-grants-2016_02
Patent number
US09249102B2

Reaction notes

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