Dimethylformamide → HCID 86599841, compound

HRID 2099015Notes

Reaction equation

HRID 2099015 reaction equation
[F:1][CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[CH:9][CH2:10][C:11]([OH:15])(O)[CH:12]=2)[CH2:7][CH2:6][CH2:5]1.O=P(Cl)(Cl)Cl.CN([CH:24]=[O:25])C>>[F:1][CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[CH:9][C:10]([CH:24]=[O:25])=[C:11]([OH:15])[CH:12]=2)[CH2:7][CH2:6][CH2:5]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 86599842HCID 86599842, compound

Product 1

HCID 86599841HCID 86599841, compoundYield 60%

Conditions

Temperature
50 °C

Procedure

290 mg (1.48 mmol) 1-(2-Fluoro-ethyl)-7-hydroxy-1,2,3,4-tetrahydro-quinolin-7-ol are dissolved in 5 mL DMF. 0.15 mL POCl3 are added dropwise at 0° C. The reaction mixture is slowly heated to 50° C., stirred an additional 3 h at this temperature, then cooled to RT and extracted with ethyl acetate and an aqueous saturated solution of sodium bicarbonate. The combined organic phases are washed with brine, dried over sodium sulphate and evaporated. The residue is column chromatographed (silica gel, ethyl acetate/petroleum ether 1:2) to yield 200 mg (60%) desired product as a brown solid.

Workup

  1. temperaturecooled to RT
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phases are washed with brine
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customchromatographed (silica gel, ethyl acetate/petroleum ether 1:2)

Sources & evidence

ORD record
ord-bfb058bc04a345f6b52a2bcd52e6febe
Source dataset
uspto-grants-2009_08
Patent number
US07569337B2

Reaction notes

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