Methanol → Methyl 6-chloropicolinate

HRID 530442Notes

Reaction equation

HRID 530442 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=1.[CH3:11]N(C=O)C.C(Cl)(=O)C(Cl)=O.CO>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 208126-Chloropicolinic acidHCID 65578Oxalyl chloride

Product 1

HCID 242723Methyl 6-chloropicolinateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Chloropyridine-2-carboxylic acid (15.0 g, 0.11 mol) was dissolved in DCM (300 mL) and DMF (1.5 mL) and oxalyl chloride (27.4 g, 0.22 mol) was added dropwise over 10 min. The reaction mixture was stirred for 1 h, MeOH (50 mL) was added dropwise over 5 min and the reaction mixture was stirred for 1.5 h. The solvents were removed in vacuo and the residue azeotroped with DCM (2×150 mL) to give the crude title compound (16.5 g, 100%) as a green solid. LCMS (ES+): 154.5 [MH]+.

Workup

  1. stirringthe reaction mixture was stirred for 1.5 h
  2. customThe solvents were removed in vacuo
  3. customthe residue azeotroped with DCM (2×150 mL)

Sources & evidence

ORD record
ord-4d44347bd2f84c08b3b5e9e8af8137c5
Source dataset
uspto-grants-2016_05
Patent number
US09353086B2

Reaction notes

Loading…