Dimethylformamide → HCID 18408340, compound

HRID 992901Notes

Reaction equation

HRID 992901 reaction equation
CN(C=O)C.[Cl:6][C:7]1[CH:12]=[C:11]([OH:13])[C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:8]=1[C:17]1[C:18](=[O:28])[N:19]([CH3:27])[C:20]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:36]([CH3:42])[C:37]([O:39][CH2:40][CH3:41])=[O:38]>O>[Cl:6][C:7]1[CH:12]=[C:11]([O:13][CH:36]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH3:42])[C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:8]=1[C:17]1[C:18](=[O:28])[N:19]([CH3:27])[C:20]([C:23]([F:24])([F:25])[F:26])=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 15457076HCID 15457076, compound

Product 1

HCID 18408340HCID 18408340, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To 10 ml of DMF, 0.8 g (2.2 mmol) of 3-(2-chloro-4-hydroxy-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2(1H)-pyridone, 0.42 g (3.0 mmol) of potassium carbonate and 0.56 g (3.3 mmol) of ethyl 2-bromopropionate were added, followed by heating and stirring at 60° C. for 2 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The organic layer was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.90 g (yield: 94%) of the desired product.

Workup

  1. temperatureby heating
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe organic layer was distilled off under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1d273edcc4fd4ffa96b6d5b42200601f
Source dataset
uspto-grants-2002_10
Patent number
US06472348B1

Reaction notes

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