Dimethylformamide → 2-Chloro-7-fluoroquinoline-3-carbaldehyde

HRID 1960011Notes

Reaction equation

HRID 1960011 reaction equation
[CH3:1][N+](C)=CCl.[Cl-:6].P(Cl)(Cl)(Cl)=O.[CH3:12][C:13]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=1)=O.CN([CH:26]=[O:27])C>>[Cl:6][C:13]1[C:12]([CH:26]=[O:27])=[CH:1][C:21]2[C:16](=[CH:17][C:18]([F:22])=[CH:19][CH:20]=2)[N:15]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 9594N-(3-Fluorophenyl)acetamideHCID 24813Phosphorus oxychlorideHCID 77311Chloro-N,N-dimethylformiminium chloride

Product 1

HCID 120991792-Chloro-7-fluoroquinoline-3-carbaldehyde

Conditions

Temperature
100 °C

Procedure

A Vilsmeier reagent prepared from DMF (23 mL) and phosphoryl chloride (78.4 mL) at 0-10° C. is slowly added dropwise to 3-fluoroacetanilide (18.5 g, 0.12 mol) and the resulting mixture is stirred at 100° C. for 14 hours. The mixture is poured onto ice-water and extracted with CH2Cl2 twice. The combined organic layer is dried, filtered and concentrated. The crystal is collected and washed with CH2Cl2 to give 2-chloro-7-fluoroquinoline-3-carbaldehyde as a brown powder.

Workup

  1. additionThe mixture is poured onto ice-water
  2. extractionextracted with CH2Cl2 twice
  3. customThe combined organic layer is dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crystal is collected
  7. washwashed with CH2Cl2

Sources & evidence

ORD record
ord-5097097849bb41509046f41c77862573
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

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