Sodium Hydroxide → 2-Chloro-5-methylnicotinic acid

HRID 275265Notes

Reaction equation

HRID 275265 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[N:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:5]=1[C:6]([O:8]C)=[O:7]>CO>[Cl:3][C:4]1[N:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:5]=1[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11636946Methyl 2-chloro-5-methylnicotinate

Product 1

HCID 123877302-Chloro-5-methylnicotinic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An aqueous solution of sodium hydroxide (9.2 g) was added to an ice-cooled, stirred solution of methyl 2-chloro-5-methylnicotinoate (35.28 g) in methanol at such a rate so that the temperature of the reaction mixture did not exceed 30° C. The mixture was then stirred at room temperature for 1.5 hours. Solvent was evaporated. The residue was diluted with water and acidified to pH 2 with concentrated hydrochloric acid. The precipitate was collected by filtration, washed with water and dried to yield the title compound as a pale yellow solid, 31.92 g, m.p. 180°-180.5° C.

Workup

  1. temperaturecooled
  2. customdid not exceed 30° C
  3. customSolvent was evaporated
  4. additionThe residue was diluted with water
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-1c34ba2235774b48ad9c639fa1fe154c
Source dataset
uspto-grants-1995_02
Patent number
US05393730

Reaction notes

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