2,6-Dichloronicotinic acid → 2-Chloro-6-methoxypyridine-3-carboxylic acid

HRID 533136Notes

Reaction equation

HRID 533136 reaction equation
C[C:2](C)([O-:4])C.[K+].[Cl:7][C:8]1[N:16]=[C:15](Cl)[CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11]>CO>[Cl:7][C:8]1[N:16]=[C:15]([O:4][CH3:2])[CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 8540472,6-Dichloronicotinic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 117692662-Chloro-6-methoxypyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

Potassium tert-butoxide (220 g, 1956 mmol) was added to a solution of 2,6-dichloronicotinic acid (180 g, 938 mmol) in MeOH (3000 mL). The mixture was stirred at 80° C. for 48 h. The solvent was evaporated in vacuo. The crude product was dissolved in H2O and treated with HCl (until the pH was 1). The solid was filtered and dried in vacuo to yield 2-chloro-6-methoxy-nicotinic acid as hydrochloride salt (130 g, 70% yield) as a white solid.

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionThe crude product was dissolved in H2O
  3. additiontreated with HCl (until the pH was 1)
  4. filtrationThe solid was filtered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-779d2318189c4477a9fc9b60a229a4fa
Source dataset
uspto-grants-2014_10
Patent number
US08853237B2

Reaction notes

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