Methanol → HCID 178521121, compound

HRID 415921Notes

Reaction equation

HRID 415921 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 C7H61NO3: 279.

Workup

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

Sources & evidence

ORD record
ord-f853882992d94fcbb4acfabce895d5d2
Source dataset
uspto-grants-2012_01
Patent number
US08088794B2

Reaction notes

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