Potassium Carbonate → 3-(1-cyano-1-methylethyl)-N-{4-methoxy-3-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide

HRID 1800483Notes

Reaction equation

HRID 1800483 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11]([C:13]([C:16]1[CH:17]=[C:18]([CH:31]=[CH:32][CH:33]=1)[C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([OH:30])[CH:23]=1)=[O:20])([CH3:15])[CH3:14])#[N:12].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C.CCCCCC>[C:11]([C:13]([C:16]1[CH:17]=[C:18]([CH:31]=[CH:32][CH:33]=1)[C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[CH:23]=1)=[O:20])([CH3:15])[CH3:14])#[N:12]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 673126173-(1-cyano-1-methylethyl)-N-(3-hydroxy-4-methoxyphenyl)benzamide

Product 1

HCID 684178733-(1-cyano-1-methylethyl)-N-{4-methoxy-3-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chloro-5-nitropyridine (547 mg, 3.45 mmol) and 3-(1-cyano-1-methylethyl)-N-(3-hydroxy-4-methoxyphenyl)benzamide (1.03 g, 3.33 mmol) in N,N-dimethylformamide (50 mL) was added potassium carbonate (1.92 g, 13.9 mmol), and the mixture was stirred at 80° C. for 4 hr. The reaction mixture was cooled to room temperature, and diluted with ethyl acetate (75 mL)/hexane (75 mL). The obtained suspension was washed with water (50 mL×3), and the combined aqueous layer was extracted with ethyl acetate (75 mL)/hexane (75 mL). The organic layer were combined, washed with saturated aqueous ammonium chloride solution (100 mL), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give 3-(1-cyano-1-methylethyl)-N-{4-methoxy-3-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide as a brown oil. This was used for the next reaction without further purification.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe obtained suspension was washed with water (50 mL×3)
  3. extractionthe combined aqueous layer was extracted with ethyl acetate (75 mL)/hexane (75 mL)
  4. washwashed with saturated aqueous ammonium chloride solution (100 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe insoluble material was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-24ae7e3c79f54f20ac9bfb77f45b7308
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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