Methanol → Methyl 2-chloro-6-methoxyisonicotinate

HRID 2040783Notes

Reaction equation

HRID 2040783 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH3:12])[N:10]=1)[C:5]([OH:7])=[O:6].[CH3:13]O>OS(O)(=O)=O>[CH3:13][O:6][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([O:11][CH3:12])[N:10]=[C:2]([Cl:1])[CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 27821242-Chloro-6-methoxypyridine-4-carboxylic acid

Product 1

HCID 13339618Methyl 2-chloro-6-methoxyisonicotinate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
65 °C

Procedure

To a suspension of 2-chloro-6-methoxy-isonicotinic acid (2.00 g, 10.7 mmol) in MeOH (100 mL), H2SO4 (2 mL) is added. The mixture is stirred at 65° C. for 20 h. The solution is cooled to rt. A precipitate forms. The solid material is collected, washed with MeOH and dried to give 2-chloro-6-methoxy-isonicotinic acid methyl ester (1.66 g) as a white solid; LC-MS: tR=1.29 min; [M+1]+=202.00.

Workup

  1. additionis added
  2. temperatureThe solution is cooled to rt
  3. customThe solid material is collected
  4. washwashed with MeOH
  5. customdried

Sources & evidence

ORD record
ord-9fa5ed80c47248ea80550dc27158facd
Source dataset
uspto-grants-2013_11
Patent number
US08580824B2

Reaction notes

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