Thionyl Chloride → 2-(Chloromethyl)-6-methoxypyridine

HRID 1694042Notes

Reaction equation

HRID 1694042 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH2:9]O)[CH:6]=[CH:5][CH:4]=1.S(Cl)([Cl:13])=O.C(=O)([O-])O.[Na+]>ClCCl>[Cl:13][CH2:9][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[N:8]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 12325389(6-Methoxypyridin-2-yl)methanol

Product 1

HCID 178542282-(Chloromethyl)-6-methoxypyridineYield 89.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of dichloromethane (5 mL) and the (6-methoxy-pyridin-2-yl)-methanol (105 mg, 0.75 mmol) described in Manufacturing Example 99-1-1 was added thionyl chloride (82.4 μL, 1.13 mmol), which was stirred for 30 minutes at room temperature. A saturated sodium hydrogencarbonate aqueous solution was added to this reaction mixture, which was then extracted with dichloromethane. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (105.8 mg, 89%).

Workup

  1. extractionwas then extracted with dichloromethane
  2. customThe organic layer was separated
  3. washwashed with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-0661be7a8809476599a7f9e4ffee7a69
Source dataset
uspto-grants-2012_04
Patent number
US08158657B2

Reaction notes

Loading…