Methanol → Methyl 2-chloro-5-(trifluoromethyl)pyridine-4-carboxylate

HRID 2386799Notes

Reaction equation

HRID 2386799 reaction equation
[C:1](Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[CH:9]=[C:10]([C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][N:16]=1)[C:11]([OH:13])=[O:12].CO>C(Cl)Cl.CN(C=O)C>[CH3:1][O:12][C:11](=[O:13])[C:10]1[C:14]([C:17]([F:20])([F:18])[F:19])=[CH:15][N:16]=[C:8]([Cl:7])[CH:9]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 65578Oxalyl chlorideHCID 112646082-Chloro-5-(trifluoromethyl)pyridine-4-carboxylic acid

Product 1

HCID 71299630Methyl 2-chloro-5-(trifluoromethyl)pyridine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (0.5 ml) was added to a solution of 2-chloro-5-(trifluoromethyl)isonicotinic acid (CAS Reg. No. 505084-58-2, 68 mg) in DCM (5 ml). DMF (1 drop) was added and the resulting mixture was stirred overnight at room temperature. Methanol (5 ml) was added and the mixture was concentrated to dryness. The crude product was used in the next step without further purification.

Workup

  1. concentrationthe mixture was concentrated to dryness
  2. customThe crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-392ec75cd9614ab18dd961e4217e665d
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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