Phosphorus oxychloride → Ethyl 2-chloro-4-(4-fluorophenyl)quinoline-3-carboxylate

HRID 1650134Notes

Reaction equation

HRID 1650134 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10](=O)[C:9]=2[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:26])=O>>[Cl:26][C:10]1[C:9]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 14780580HCID 14780580, compound

Product 1

HCID 14780581Ethyl 2-chloro-4-(4-fluorophenyl)quinoline-3-carboxylate

Procedure

Ethyl 4-(4-fluorophenyl)-1,2-dihydro-2-oxo-3-quinolinecarboxylate (12.8 g) is dissolved in 40 ml of phosphorus oxychloride under an atmosphere of nitrogen. The resulting solution is refluxed one hour, cooled, concentrated, and the residue neutralized with cold 1N sodium hydroxide solution and extracted with ethyl acetate. The organic extracts are filtered through a bed of silica to give 13.2 g of ethyl 2-chloro-4-(4-fluorophenyl)-3-quinolinecarboxylate as a white solid; mp 113°-114° C.; 1H NMR (chloroform-d): δ 8.02 (d, 1H), 7.75-7.70 (m, 1H), 7.52-7.43 (m, 2H), 7.34-7.28 (m, 2H), 7.20-7.12 (m, H), 4.14-4.07 (q, 2H), 1.02 (t, 3H) ppm.

Workup

  1. temperatureThe resulting solution is refluxed one hour
  2. temperaturecooled
  3. concentrationconcentrated
  4. extractionthe residue neutralized with cold 1N sodium hydroxide solution and extracted with ethyl acetate
  5. filtrationThe organic extracts are filtered through a bed of silica

Sources & evidence

ORD record
ord-99126579e9144c00802679126820f422
Source dataset
uspto-grants-1990_05
Patent number
US04923861

Reaction notes

Loading…