Water → 1-Ethyl-3-(2-methoxy-4-nitrophenyl)pyridin-2(1H)-one

HRID 218522Notes

Reaction equation

HRID 218522 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[C:12]1[C:13](=[O:18])[NH:14][CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:26][CH3:27].O>CN(C=O)C>[CH2:26]([N:14]1[CH:15]=[CH:16][CH:17]=[C:12]([C:4]2[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]=2[O:2][CH3:1])[C:13]1=[O:18])[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 595867673-(2-Methoxy-4-nitrophenyl)pyridin-2(1H)-one

Product 1

HCID 595867171-Ethyl-3-(2-methoxy-4-nitrophenyl)pyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

350 mg (1.42 mmol) of the product from example 55A are suspended in 3.5 ml of DMF. To this are added 393 mg (2.84 mmol) of potassium carbonate and 266 mg (1.71 mmol) of iodoethane, and the mixture is left to stir at RT for 3 h. Then it is admixed with water and extracted with dichloromethane. The organic solution is dried over sodium sulfate, concentrated and purified by preparative HPLC. This affords 224 mg (57% of theory) of the title compound.

Workup

  1. waitthe mixture is left
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic solution is dried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-22deb0e9c8cb406cbc008ac388982d1f
Source dataset
uspto-grants-2012_06
Patent number
US08198267B2

Reaction notes

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