Ethyl Acetate → HCID 67413505, compound

HRID 2366777Notes

Reaction equation

HRID 2366777 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[NH2:11][C:12]1[CH:13]=[C:14]([OH:19])[CH:15]=[CH:16][C:17]=1[Cl:18].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[Cl:18][C:17]1[CH:16]=[CH:15][C:14]([O:19][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)=[CH:13][C:12]=1[NH2:11]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 50700783-Amino-4-chlorophenol

Product 1

HCID 67413505HCID 67413505, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-5-nitropyridine (4.76 g, 30 mmol) and 3-amino-4-chlorophenol (4.31 g, 30 mmol) in N,N-dimethylformamide (15 mL) was added potassium carbonate (4.15 g, 30 mmol), and the mixture was stirred at room temperature for 16 hr. Ethyl acetate (80 mL) was added to the reaction mixture, and the mixture was washed successively with water (50 mL) and saturated brine (50 mL). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residual solid was recrystallized from ethyl acetate (15 mL)/n-hexane (15 mL), and the precipitated crystals were collected by filtration, washed with diisopropyl ether (20 mL) and dried under reduced pressure to give the title compound (6.74 g, 85%) as brownish-red crystals.

Workup

  1. washthe mixture was washed successively with water (50 mL) and saturated brine (50 mL)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residual solid was recrystallized from ethyl acetate (15 mL)/n-hexane (15 mL)
  5. filtrationthe precipitated crystals were collected by filtration
  6. washwashed with diisopropyl ether (20 mL)
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-8d71bb59fa564d5fb17ebb005f15103b
Source dataset
uspto-grants-2014_04
Patent number
US08697874B2

Reaction notes

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