Thionyl Chloride → 4-(Chloromethyl)-[1,3]dioxolo[4,5-c]pyridine

HRID 1647172Notes

Reaction equation

HRID 1647172 reaction equation
O[CH2:2][C:3]1[C:8]2[O:9][CH2:10][O:11][C:7]=2[CH:6]=[CH:5][N:4]=1.S(Cl)([Cl:14])=O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[Cl:14][CH2:2][C:3]1[C:8]2[O:9][CH2:10][O:11][C:7]=2[CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 199264631,3-Dioxolo[4,5-C]pyridine-4-methanol

Product 1

HCID 199264524-(Chloromethyl)-[1,3]dioxolo[4,5-c]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Hydroxymethyl-3,4-methylenedioxypyridine (90 mg, 0.59 mmol) was dissolved in methylene chloride (10 ml) and thionyl chloride (240 mg, 2 mmol) was added. After 10 min at ambient temperature the mixture was hydrolysed with sodium hydrogen carbonate and the phases were separated. The organic phase was dried over sodium sulphate, filtered and concentrated under reduced pressure. Yield: 90 mg (88%) of the title compound (crude).

Workup

  1. customthe phases were separated
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-36292afafd164e378e21d66a54f93554
Source dataset
uspto-grants-1995_07
Patent number
US05430042

Reaction notes

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