Hydrochloric Acid → 3-Pyridinol,6-chloro-2-methyl-(9CI)

HRID 1931566Notes

Reaction equation

HRID 1931566 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([O:9]C(=O)C)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>>[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([OH:9])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86636108HCID 86636108, compound

Product 1

HCID 450796993-Pyridinol,6-chloro-2-methyl-(9CI)Yield 96.3%

Conditions

Temperature
0 °C

Procedure

A mixture of acetic acid 6-chloro-2-methyl-pyridin-3-yl ester (316 mg, 1.7 mmol) and 15% aqueous sodium hydroxide (2.5 mL) was stirred at 0° C. for 15 min and then at room temperature for 1 h. 1 M HCl (12 mL) was added and the mixture was extracted 4 times with ethyl acetate. The ethyl acetate was evaporated to give 6-chloro-2-methyl-pyridin-3-ol (235 mg, 96%) as a white powder. 1H NMR (300 MHz, DMSO-d6) δ 2.26 (s, 3H), 7.09 (d, 1H, J=8.4 Hz), 7.14 (d, 1H, J=8.4 Hz), 10.08 (br s, 1H).

Workup

  1. waitat room temperature for 1 h
  2. extractionthe mixture was extracted 4 times with ethyl acetate
  3. customThe ethyl acetate was evaporated

Sources & evidence

ORD record
ord-c3fd64886cba46a6a38282298685f179
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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