Water → HCID 18673889, compound

HRID 1635974Notes

Reaction equation

HRID 1635974 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].Cl[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[N+:19]([C:16]1[CH:17]=[CH:18][C:13]([O:1][C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH2:4][CH2:5][C:6]3=[O:11])=[N:14][CH:15]=1)([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 5905474-Hydroxy-1-indanone

Product 1

HCID 18673889HCID 18673889, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.0 g of 4-hydroxy-1-indanone, 1.07 g of 2-chloro-5-nitropyridine and 5 g of anhydrous potassium carbonate were dissolved in 10 ml of N,N-dimethylformamide (DMF) and the mixture was stirred at room temperature for 17 hours. After the completion of the reaction, 50 ml of water was added to the reaction solution and the solution was extracted with ethyl acetate. After the organic (ethyl acetate) layer was washed with water and dried over anhydrous sodium sulfate, the solvent was distilled off. The resulting residue was recrystallized from ethyl acetate to obtain the titled compound (1.36 g, pale yellow powder).

Workup

  1. additionwas added to the reaction solution
  2. extractionthe solution was extracted with ethyl acetate
  3. washAfter the organic (ethyl acetate) layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off
  6. customThe resulting residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1c6be59f4a3e47a299d1e3e875018e28
Source dataset
uspto-grants-2003_01
Patent number
US06511995B1

Reaction notes

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