Methanol → HCID 178498694, compound

HRID 415922Notes

Reaction equation

HRID 415922 reaction equation
[OH:1][C:2]1[N:10]=[CH:9][CH:8]=[C:7]([I:11])[C:3]=1[C:4](Cl)=[O:5].[CH3:12][OH:13]>>[OH:1][C:2]1[N:10]=[CH:9][CH:8]=[C:7]([I:11])[C:3]=1[C:4]([O:13][CH3:12])=[O:5]

Participants

3

Reactant 2

HCID 887MethanolHCID 178521121HCID 178521121, compound

Product 1

HCID 178498694HCID 178498694, compound

Procedure

Thionyl chloride (3.81 ml, 52.2 mmol) was added to a suspension of 2-hydroxy-4-iodonicotinic acid (3.46 g, 13.1 mmol) in dichloromethane (12 mL) in a pressure vessel at room temperature. The reaction mixture was then heated at 75° C. for 3 h. An aliquot was taken and hydrolyzed with methanol. LCMS analysis showed the derived methyl ester seen as major compound. The reaction mixture was cooled to room temperature and was concentrated in vacuo to give 2-hydroxy-4-iodonicotinoyl chloride. 2-hydroxy-4-iodonicotinoyl chloride in MeOH (100 mL) was stirred at room temperature for 2 h. Concentration in vacuo of the reaction mixture afforded methyl 2-hydroxy-4-iodonicotinate (3.64 g, 13.1 mmol, quantitative yield). MS (ESI pos. ion) m/z: 280 (MH+). Calc'd exact mass for C7H61NO3: 279.

Workup

  1. concentrationConcentration in vacuo of the reaction mixture

Sources & evidence

ORD record
ord-5b70f00020f548e8bd8d1e5c45ba92bc
Source dataset
uspto-grants-2012_01
Patent number
US08088794B2

Reaction notes

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