Oxalyl chloride → 6-(4-Fluorophenyl)-2-methyl-3-pyridinecarbonyl chloride

HRID 534730Notes

Reaction equation

HRID 534730 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([CH3:14])[C:11]([C:15]([OH:17])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:21])=O>C(Cl)Cl.CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([CH3:14])[C:11]([C:15]([Cl:21])=[O:17])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 242777906-(4-Fluorophenyl)-2-methylpyridine-3-carboxylic acid

Product 1

HCID 866181086-(4-Fluorophenyl)-2-methyl-3-pyridinecarbonyl chlorideYield 41.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

6-(4-Fluorophenyl)-2-methyl-3-pyridinecarboxylic acid (0.2 g, 0.866 mol) was suspended in DCM (14 mL) and DMF (1 drop) was added. The mixture was cooled in an ice-bath and oxalyl chloride (0.226 mL, 2.598 mmol) was added portion wise over 5 minutes. The mixture was heated to 40° C. for 90 minutes. The mixture was allowed to cool and the solvent removed under vacuum to give 6-(4-fluorophenyl)-2-methyl-3-pyridinecarbonyl chloride as a yellow solid (0.270 g) which was used directly in step 2.

Workup

  1. temperatureThe mixture was cooled in an ice-bath
  2. temperatureto cool
  3. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-b7ae2b929ab24665b00a7e426d28de59
Source dataset
uspto-grants-2014_10
Patent number
US08853218B2

Reaction notes

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