Methanol → Methyl pyridine-3-acetate

HRID 1475467

Reaction equation

HRID 1475467 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:3]=1.S(Cl)(Cl)=O.[CH3:16]O>>[CH3:16][O:10][C:9](=[O:11])[CH2:8][C:4]1[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 27237243-Pyridineacetic acid, hydrochloride (1:1)

Product 1

HCID 96475Methyl pyridine-3-acetate

Procedure

A solution of pyridin-3-yl-acetic acid hydrochloride (10 g, 57.6 mmol) in MeOH (30 mL) was treated with thionyl chloride (4.2 mL, 57.6 mmol) and the mixture was stirred at room temperature for 2 h. Solvent was removed in vacuo and the residue was partitioned between saturated aqueous NaHCO3 and EtOAc. The organic phase was collected, dried over MgSO4 and evaporated to give the title compound (7.9 g) as a colourless oil. 1H NMR (CDCl3): 8.53 (2H, m), 7.64 (1H, d), 7.33-7.20 (1H, m), 3.72 (3H, s), 3.64 (2H, s).

Workup

  1. customSolvent was removed in vacuo
  2. customthe residue was partitioned between saturated aqueous NaHCO3 and EtOAc
  3. customThe organic phase was collected
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-6c99a33576f245fca458856b513e8d9a
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Linked notes

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