Water → 1-(5-Chloro-2-methyl-4-nitrophenyl)-3-methylpyridin-2(1H)-one

HRID 218537

Reaction equation

HRID 218537 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.CC(C)([O-])C.[K+].[Cl:15][C:16]1[CH:21]=[C:20](F)[C:19]([CH3:23])=[CH:18][C:17]=1[N+:24]([O-:26])=[O:25].O>CN(C=O)C>[Cl:15][C:16]1[C:17]([N+:24]([O-:26])=[O:25])=[CH:18][C:19]([CH3:23])=[C:20]([N:3]2[CH:4]=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]2=[O:1])[CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 875934-Chloro-2-fluoro-5-nitrotolueneHCID 23665647Potassium tert-butoxideHCID 178426317HCID 178426317, compound

Product 1

HCID 595866951-(5-Chloro-2-methyl-4-nitrophenyl)-3-methylpyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.50 g (13.8 mmol) of 2-hydroxy-3-methylpyridine in 70 ml of DMF are admixed at 0° C. with 2.31 g (20.6 mmol) of potassium tert-butoxide, and the mixture is stirred at room temperature for 30 min. 2.87 g (15.1 mmol) of 2-chloro-4-fluoro-5-methylnitrobenzene are added while continuing to stir at RT. After 17 h, the mixture is admixed with 1000 ml of water and then extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulfate and, after filtration, the solvents are removed under reduced pressure. The residue is purified by chromatography on silica gel (2:1 cyclohexane/ethyl acetate). This affords 2.15 g (56% of theory) of the desired compound.

Workup

  1. stirringto stir at RT
  2. waitAfter 17 h
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. filtrationafter filtration
  6. customthe solvents are removed under reduced pressure
  7. customThe residue is purified by chromatography on silica gel (2:1 cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-babfbf2138ce4c39855e0fa8fe8bc918
Source dataset
uspto-grants-2012_06
Patent number
US08198267B2

Linked notes

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