Phosphorus oxychloride → 2-Chloro-4-(4-fluorophenyl)-7-methylquinoline

HRID 2422549Notes

Reaction equation

HRID 2422549 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([CH3:18])=[CH:15][CH:16]=3)[N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:21])=O.C([O-])(O)=O.[Na+]>>[Cl:21][C:10]1[CH:9]=[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][C:14]([CH3:18])=[CH:15][CH:16]=2)[N:11]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 574378424-(4-Fluorophenyl)-7-methylquinoline

Product 1

HCID 866219782-Chloro-4-(4-fluorophenyl)-7-methylquinoline

Procedure

A solution of 4-(4-fluorophenyl)-7-methylquinoline (3.09 g, 12.2 mmol) in phosphorus oxychloride (8 mL, 85.8 mmol) was stirred 30 min. at 90° C. The mixture was poured slowly into an aqueous saturated solution of NaHCO3 and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduce pressure. Purification on silica gel (eluting with acetone/dichloromethane/hexanes, 1:70:29) gave the title compound. MS (+ESI): 271 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification on silica gel (eluting with acetone/dichloromethane/hexanes, 1:70:29)

Sources & evidence

ORD record
ord-70b02feae16d4e10bec38f51d393c9a6
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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