Thionyl Chloride → Ethyl 5-chloro-6-(chloromethyl)pyridine-3-carboxylate--hydrogen chloride (1/1)

HRID 715443Notes

Reaction equation

HRID 715443 reaction equation
[Cl:1][C:2]1[C:3]([CH2:13]O)=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].S(Cl)([Cl:17])=O>C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[C:3]([CH2:13][Cl:17])=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 89875094HCID 89875094, compound

Product 1

HCID 71744190Ethyl 5-chloro-6-(chloromethyl)pyridine-3-carboxylate--hydrogen chloride (1/1)Yield 193.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 5-chloro-6-(hydroxymethyl)nicotinate (990 mg, 4.59 mmol, Step-2) in DCM (20 mL) is added thionyl chloride (0.80 mL, 9.2 mmol) at 0° C. After stirring at rt for 2 hours, the solvent is removed in vacuo to give 1.20 g (97% yield) of the title compound as brown oil.

Workup

  1. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-05701a66edbc459bba2e38445538cce1
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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