Sodium Hydroxide → 6-Chloro-2-methoxypyridine-3-carboxylic acid

HRID 372210Notes

Reaction equation

HRID 372210 reaction equation
[CH3:1][O:2][C:3]1[N:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:4]=1[C:5]([O:7]C)=[O:6].[OH-].[Na+]>CO>[CH3:1][O:2][C:3]1[N:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:4]=1[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10560015Methyl 6-chloro-2-methoxynicotinate

Product 1

HCID 203288056-Chloro-2-methoxypyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 10.1 g (0.05 mole) of methyl 2-methoxy-6-chloronicotinate in 20 ml of methanol is added dropwise at 70° C in the course of 30 minutes to 500 ml of 0.1 N aqueous sodium hydroxide solution. After completion of the addition, the mixture is refluxed for 1 hour. The clear solution is concentrated in vacuo to approx. 100 ml and acidified with 2 N hydrochloric acid to pH 3. The precipitate which has formed is collected by filtration, washed with a small amount of water and dried. The residue is recrystallized from benzene-petroleum ether to yield pure 2-methoxy-6-chloronicotinic acid with a melting point of 210°-215° C.

Workup

  1. additionAfter completion of the addition
  2. temperaturethe mixture is refluxed for 1 hour
  3. concentrationThe clear solution is concentrated in vacuo to approx. 100 ml
  4. customThe precipitate which has formed
  5. filtrationis collected by filtration
  6. washwashed with a small amount of water
  7. customdried
  8. customThe residue is recrystallized from benzene-petroleum ether

Sources & evidence

ORD record
ord-ecbe1326b99343859b065919e760bee9
Source dataset
uspto-grants-1978_05
Patent number
US04089960

Reaction notes

Loading…