Potassium Hydroxide → Potassium 6-chloro-3-methyl-pyridine-2-carboxylate

HRID 239915Notes

Reaction equation

HRID 239915 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10]C)=[O:9])[C:5]([CH3:12])=[CH:4][CH:3]=1.[OH-].[K+:14]>C(O)(C)C>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O-:10])=[O:9])[C:5]([CH3:12])=[CH:4][CH:3]=1.[K+:14]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 45489870Methyl 6-chloro-3-methylpyridine-2-carboxylate

Product 1

HCID 86707308Potassium 6-chloro-3-methyl-pyridine-2-carboxylateYield 92.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Methyl 6-chloro-3-methyl-pyridine-2-carboxylate (50 g, 269.4 mmoles) is added to a solution of potassium hydroxide (18.7 g, 282.9 mmoles) in isopropyl alcohol (2000 mL). The mixture is stirred at ambient temperature for 1 hour. Hexanes (500 mL) are added, and the solid is filtered, washed with hexanes, and dried under reduced pressure at 45° C. for 4 hours to give the title compound (52 g, 92%). Mass spectrum (m/z): 172.0 (M+1). 1H NMR (300 MHz, D2O): 7.62 (d, J=8.0 Hz, 1H), 7.27 (d, J=8.0 Hz, 1H), 2.23 (s, 3H).

Workup

  1. filtrationthe solid is filtered
  2. washwashed with hexanes
  3. customdried under reduced pressure at 45° C. for 4 hours

Sources & evidence

ORD record
ord-76c7e21f34624ca88aad9ae7b16a9f52
Source dataset
uspto-grants-2014_02
Patent number
US08642768B2

Reaction notes

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