Phosphorus oxychloride → 2-Chloro-4-(3-fluorophenyl)-6-methoxyquinoline-3-carbonitrile

HRID 640719Notes

Reaction equation

HRID 640719 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=3)[NH:11][C:10](=O)[C:9]=2[C:21]#[N:22])[CH:5]=[CH:6][CH:7]=1.O=P(Cl)(Cl)[Cl:25]>CCOC(C)=O>[Cl:25][C:10]1[C:9]([C:21]#[N:22])=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[N:11]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 114151654-(3-Fluorophenyl)-6-methoxy-2-oxo-1,2-dihydroquinoline-3-carbonitrile

Product 1

HCID 113703952-Chloro-4-(3-fluorophenyl)-6-methoxyquinoline-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(3-fluorophenyl)-6-methoxy-2-oxo-1,2-dihydroquinoline-3-carbonitrile (1.10 g, 3.74 mmol) in 30 mL of phosphorus oxytrichloride was heated in a sealed pressure tube at 90° C. for 2 hours. The solution was cooled to room temperature and allowed to stand overnight. The mixture was diluted with EtOAc, cooled to 0° C., and quenched by the careful addition of saturated NaHCO3 solution. The organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to provide the titled compound. ESI+ MS: 313.0 [M+H]+.

Workup

  1. temperaturecooled to 0° C.
  2. customquenched by the careful addition of saturated NaHCO3 solution
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-332b833ff8ab48c78d65f4648032dc41
Source dataset
uspto-grants-2010_04
Patent number
US07692017B2

Reaction notes

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