Thionyl Chloride → Methyl 6-(chloromethyl)nicotinate

HRID 2355283Notes

Reaction equation

HRID 2355283 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]O)=[N:6][CH:5]=1.S(Cl)([Cl:15])=O>ClCCl>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][Cl:15])=[N:6][CH:5]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 7894146-Hydroxymethyl-nicotinic acid methyl ester

Product 1

HCID 15331516Methyl 6-(chloromethyl)nicotinateYield 122%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Add 6-hydroxymethyl-nicotinic acid methyl ester (9.6 g, 57.4 mmol) and dichloromethane (200 mL) to a flask and cool to 0° C. Add thionyl chloride (10.25 g, 86.14 mmol). Stir the mixture at room temperature for 1 hr. Concentrate the reaction mixture under reduce pressure to give the crude 6-chloromethyl-nicotinic acid methyl ester (13 g, 102% yield) as a yellow solid. MS (m/z): 223 (M+1).

Workup

  1. concentrationConcentrate the reaction mixture

Sources & evidence

ORD record
ord-a27b4b4a2d784592bc707f7095216c6f
Source dataset
uspto-grants-2010_07
Patent number
US07754742B2

Reaction notes

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