Methanol → HCID 67086052, compound

HRID 1911026Notes

Reaction equation

HRID 1911026 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.S(Cl)([Cl:13])=O.[CH3:15]O>>[ClH:13].[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:15])=[O:9])=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2687405-Hydroxypyridine-2-carboxylic acid

Product 1

HCID 67086052HCID 67086052, compoundYield 100%

Conditions

Temperature
60 °C

Procedure

To solution of 5-hydroxypicolinic acid (820 mg, 5.89 mmol) in methanol (20 mL) was dropwise added thionyl chloride (0.430 mL, 5.89 mmol) at rt. The mixture was stirred at 60° C. for 20 h. The mixture was concentrated in vacuo to give a crude methyl 5-hydroxypicolinate hydrochloride (1.12 g, 5.89 mmol, 100% yield), which was used for the next step without purification. LCMS (M+H)+=154.01. 1H NMR (500 HMz, methanol-d4) δ 8.45 (d, J=6.0 Hz, 2H), 8.08 (dd, J=9.0, 2.3 Hz, 1H), 4.09 (s, 3H)

Workup

  1. customat rt
  2. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-e327ef70bb4944f390d34746e0604a67
Source dataset
uspto-grants-2013_12
Patent number
US08604024B2

Reaction notes

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