Potassium Carbonate → HCID 18402987, compound

HRID 1800539Notes

Reaction equation

HRID 1800539 reaction equation
[NH2:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([Cl:9])=[C:6]([OH:8])[CH:7]=1.Cl[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O>[Cl:9][C:5]1[C:6]([O:8][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=2)=[CH:7][C:2]([NH2:1])=[C:3]([F:10])[CH:4]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 783082-Chloro-5-nitropyridineHCID 1586545-Amino-2-chloro-4-fluorophenol

Product 1

HCID 18402987HCID 18402987, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-amino-2-chloro-4-fluorophenol (5.00 g, 30.9 mmol), 2-chloro-5-nitropyridine (5.09 g, 32.1 mmol), potassium carbonate (4.51 g, 32.6 mmol) and N,N-dimethylformamide (50 mL) was stirred at room temperature for 13 hr. To the reaction mixture was added aqueous ammonium chloride solution (50 mL), and the mixture was extracted with ethyl acetate (80 mL×3). The organic layer was washed with water (50 mL) and saturated brine (30 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The precipitate was collected by filtration to give the title compound (6.31 g, 72%) as a yellow powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (80 mL×3)
  2. washThe organic layer was washed with water (50 mL) and saturated brine (30 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-730eec7922ac45778dd434b04872d0d5
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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