Ethyl Acetate → HCID 67413505, compound

HRID 1800625Notes

Reaction equation

HRID 1800625 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. To the reaction mixture was added ethyl acetate (80 mL), 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 brown 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-3ee5a91dc8b84256a10c17872c95a153
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

Loading…