Hydrochloric Acid → 6-Chloro-4-iodopyridin-3-ol

HRID 422100Notes

Reaction equation

HRID 422100 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([I:8])[C:5]([O:9]COC)=[CH:4][N:3]=1.Cl.C(=O)(O)[O-].[Na+]>C1COCC1>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([OH:9])=[C:6]([I:8])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 587641152-Chloro-4-iodo-5-(methoxymethoxy)pyridine

Product 1

HCID 533020386-Chloro-4-iodopyridin-3-olYield 98.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Treat a solution of 2-chloro-4-iodo-5-methoxymethoxy-pyridine (8.1 g, 27 mmol) in THF (40 mL) with 3 N HCl (61 mL). Heat the resulting mixture to 60° C. for 3 hours. Cool the mixture to room temperature and adjust the pH to 7 by the slow addition of saturated aqueous sodium bicarbonate solution. Extract the mixture with three portions of ethyl acetate. Combine the organic extracts and dry over sodium sulfate, filter, and concentrate in vacuo to give the title compound (6.8 g, 98%) as a brown solid used without further purification. 1H NMR (400 MHz, DMSO-d6) δ 11.04 (s, 1H), 7.81-7.87 (m, 2H).

Workup

  1. temperatureCool the mixture to room temperature
  2. extractionExtract the mixture with three portions of ethyl acetate
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-b1709d98f9d242808313649be2936f13
Source dataset
uspto-grants-2012_01
Patent number
US08101628B2

Reaction notes

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