Thionyl Chloride → HCID 59527509, compound

HRID 384436Notes

Reaction equation

HRID 384436 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:19])[CH:17]=2)[N:12]=[C:11]([CH2:20]O)[C:10]=1[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:25])=O>C1COCC1.C1(C)C=CC=CC=1.N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:19])[CH:17]=2)[N:12]=[C:11]([CH2:20][Cl:25])[C:10]=1[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 24386Thionyl ChlorideHCID 59527017HCID 59527017, compound

Product 1

HCID 59527509HCID 59527509, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

[4-(Benzyloxy)-6-fluoro-3-methylquinolin-2-yl]methanol (4.02 g) was dissolved in THF (50 mL) and toluene (50 mL), and 10 drops of pyridine were added thereto. Thionyl chloride (1.50 mL) was gradually added dropwise thereto under ice-cooling, and the reaction mixture was stirred at the same temperature for 1 hour, and further stirred at room temperature for 1 hour. After the precipitated solid was collected by filtration, ethyl acetate and a saturated aqueous sodium hydrogen carbonate solution were gradually added with stirring to the filtrate under ice-cooling. After the foaming became stable, the organic layer was separated, washed sequentially with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated. The residue was purified by silica gel column chromatography (eluent: chloroform) to obtain 4-(benzyloxy)-2-(chloromethyl)-6-fluoro-3-methylquinoline (3.85 g).

Workup

  1. temperatureunder ice-cooling
  2. stirringfurther stirred at room temperature for 1 hour
  3. filtrationAfter the precipitated solid was collected by filtration, ethyl acetate
  4. additiona saturated aqueous sodium hydrogen carbonate solution were gradually added
  5. stirringwith stirring to the filtrate under ice-
  6. temperaturecooling
  7. customthe organic layer was separated
  8. washwashed sequentially with water and saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent was evaporated
  11. customThe residue was purified by silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-9bbb5d6b2e47442b869dab4c62579224
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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