Potassium Carbonate → 6-Chloro-5-methylpyridin-3-ol

HRID 930486Notes

Reaction equation

HRID 930486 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][C:11]1[CH:12]=[N:13][C:14]([Cl:18])=[C:15]([CH3:17])[CH:16]=1)(=O)C>CO>[Cl:18][C:14]1[N:13]=[CH:12][C:11]([OH:10])=[CH:16][C:15]=1[CH3:17]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 218288696-Chloro-5-methylpyridin-3-yl acetate

Product 1

HCID 128520156-Chloro-5-methylpyridin-3-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (1.10 g, 0.0081 mol) was added to a stirred solution of 6-chloro-5-methylpyridine-3-yl acetate (750 mg, 0.004 mol) in MeOH (15 mL) at ambient temperature. The reaction mixture was stirred for 1 h at ambient temperature. The reaction mixture was concentrated under reduced pressure and the residue was diluted with minimum amounts of water and neutralized with 1N HCl (15 mL). After neutralization, the solution was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated to give 6-chloro-5-methylpyridine-3-ol as an off white solid (500 mg, 89%). MS m/z=143.01 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with minimum amounts of water and neutralized with 1N HCl (15 mL)
  3. extractionAfter neutralization, the solution was extracted with ethyl acetate (2×100 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-11b1e41e244941babda06339b629afd3
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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