Hydrochloric Acid → HCID 70874044, compound

HRID 1526118Notes

Reaction equation

HRID 1526118 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([CH:16]=[C:17]([F:19])[CH:18]=1)[C:7]([C:9]1[C:10](=[O:15])[NH:11][CH:12]=[CH:13][CH:14]=1)=[O:8].I[CH2:21][CH3:22].Cl>CN(C)C=O>[F:19][C:17]1[CH:16]=[C:6]([CH:5]=[C:4]([F:3])[CH:18]=1)[C:7]([C:9]1[C:10](=[O:15])[N:11]([CH2:21][CH3:22])[CH:12]=[CH:13][CH:14]=1)=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 70874345HCID 70874345, compound

Product 1

HCID 70874044HCID 70874044, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

187 mg (4.68 mmol) of sodium hydride 60% dispersion in oil is added to 0.44 g (1.87 mmol) of 3-(3,5-difluorobenzoyl)pyridin-2(1H)-one dissolved in 15 ml of anhydrous dimethylformamide at 0° C. 379 mg (2.43 mmol) of iodoethane is added to this mixture. The reaction mixture is stirred at 0° C. for 10 minutes and then for 1 hour at room temperature. 1 N HCl solution is added and then the product is extracted several times with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution, dried on magnesium sulfate and concentrated. The residue is purified by silica gel chromatography (eluent: 10:1 dichloromethane/methanol) to yield 221 mg (50%) of 3-(3,5-difluorobenzoyl)-1-ethylpyridin-2(1H)-one in the form of a yellow solid.

Workup

  1. waitfor 1 hour at room temperature
  2. extractionthe product is extracted several times with ethyl acetate
  3. washwashed with saturated sodium chloride solution
  4. customdried on magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue is purified by silica gel chromatography (eluent: 10:1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-fb3f63c13bdd42aa843175d92c16182d
Source dataset
uspto-grants-2015_07
Patent number
US09085575B2

Reaction notes

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