Acetic Acid → Methyl 2-chloro-6-(2-methoxyphenyl)pyridine-3-carboxylate

HRID 1183002Notes

Reaction equation

HRID 1183002 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])[N:3]=1.[CH3:19][Si](C=[N+]=[N-])(C)C.C(O)(=O)C>CO.C1(C)C=CC=CC=1.CCCCCC>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH3:19])=[O:9])=[CH:6][CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])[N:3]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 167693TrimethylsilyldiazomethaneHCID 8285042-Chloro-6-(2-methoxyphenyl)nicotinic acid

Product 1

HCID 58379299Methyl 2-chloro-6-(2-methoxyphenyl)pyridine-3-carboxylate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

500 mg (1.90 mmol) of 2-chloro-6-(2-methoxyphenyl)pyridine-3-carboxylic acid were initially charged in a mixture of 20 ml of methanol and 8 ml of toluene and admixed with 8 ml (16 mmol) of a 2 molar solution of trimethylsilyldiazomethane in hexane. The mixture was stirred at RT for 15 h and then 1 ml of acetic acid was added. The solvent was removed fully under reduced pressure, and the resulting solid was used without further purification. 502 mg (87% of theory) of the product were obtained.

Workup

  1. customThe solvent was removed fully under reduced pressure
  2. customthe resulting solid was used without further purification
  3. custom502 mg (87% of theory) of the product were obtained

Sources & evidence

ORD record
ord-b5deab253eee45569d5128370d3f9e26
Source dataset
uspto-grants-2014_03
Patent number
US08664246B2

Reaction notes

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