Sodium Hydroxide → 6-Chloro-2,4-dimethylnicotinic acid

HRID 1782556Notes

Reaction equation

HRID 1782556 reaction equation
C([O:3][C:4](=[O:14])[C:5]1[C:10]([CH3:11])=[CH:9][C:8]([Cl:12])=[N:7][C:6]=1[CH3:13])C.[OH-].[Na+]>CCO>[Cl:12][C:8]1[CH:9]=[C:10]([CH3:11])[C:5]([C:4]([OH:14])=[O:3])=[C:6]([CH3:13])[N:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71721008Ethyl 6-chloro-2,4-dimethylnicotinate

Product 1

HCID 34465636-Chloro-2,4-dimethylnicotinic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
90 °C

Procedure

To a solution of 6-chloro-2,4-dimethyl-nicotinic acid ethyl ester (0.200 g, 0.930 mmol) in EtOH (1 mL) was added 4N NaOH (1 mL), and the mixture was heated at 90° C. for 1 h. After the mixture was cooled to room temperature EtOH was removed and the aqueous residue was acidified with 4N HCl to afford a white precipitate. The precipitate (0.152 g, 88%) was collected by filtration and dried under vacuum to give 6-chloro-2,4-dimethyl-nicotinic acid as a white solid. 1H NMR (CD3OD) δ 2.37 (s, 3H), 2.51 (s, 3H), 7.23 (s, 1H).

Workup

  1. customwas removed
  2. customto afford a white precipitate
  3. filtrationThe precipitate (0.152 g, 88%) was collected by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-b3d9903ac92242edb1c9ff9725e0d4ba
Source dataset
uspto-grants-2009_03
Patent number
US07498346B2

Reaction notes

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