Methanol → HCID 178521121, compound

HRID 2359708Notes

Reaction equation

HRID 2359708 reaction equation
S(Cl)([Cl:3])=O.[OH:5][C:6]1[N:14]=[CH:13][CH:12]=[C:11]([I:15])[C:7]=1[C:8](O)=[O:9].CO>ClCCl>[OH:5][C:6]1[N:14]=[CH:13][CH:12]=[C:11]([I:15])[C:7]=1[C:8]([Cl:3])=[O:9]

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 178524664HCID 178524664, compound

Product 1

HCID 178521121HCID 178521121, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
75 °C

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 C7H6INO3: 279.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-0d98dffb8a3c4034911da37a96bd55d3
Source dataset
uspto-grants-2014_04
Patent number
US08685983B2

Reaction notes

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