Sodium Hydroxide → HCID 57387083, compound

HRID 1800658Notes

Reaction equation

HRID 1800658 reaction equation
[Cl:1][C:2]1[C:27]([C:28]2([C:31]#[N:32])[CH2:30][CH2:29]2)=[CH:26][CH:25]=[CH:24][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[C:11]([O:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][N:15]=2)[CH:10]=[CH:9][C:8]=1[F:23])=[O:5].[Cl-].[Ca+2].[Cl-].[OH-].[Na+]>C(OCC)(=O)C.O.C(O)C>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([O:13][C:11]2[CH:10]=[CH:9][C:8]([F:23])=[C:7]([NH:6][C:4](=[O:5])[C:3]3[CH:24]=[CH:25][CH:26]=[C:27]([C:28]4([C:31]#[N:32])[CH2:29][CH2:30]4)[C:2]=3[Cl:1])[CH:12]=2)=[N:15][CH:16]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 5284359Calcium ChlorideHCID 573842802-chloro-3-(1-cyanocyclopropyl)-N-{2-fluoro-5-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide

Product 1

HCID 57387083HCID 57387083, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-chloro-3-(1-cyanocyclopropyl)-N-{2-fluoro-5-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide (6.60 g, 14.6 mmol), reduced iron (1.68 g, 30.0 mmol), calcium chloride (3.33 g, 30.0 mmol), water (80 mL) and ethanol (20 mL) was stirred at 80° C. for 18 hr. The mixture was cooled to room temperature, water (250 mL), 1N aqueous sodium hydroxide solution (250 mL), ethyl acetate (300 mL) and celite (50 g) were added, and the mixture was stirred. The mixture was filtered through celite, and the insoluble material was washed with ethyl acetate (100 mL). The organic layer was separated, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was crystallized from diethyl ether to give the title compound (4.23 g, 69%) as a pale-yellow powder.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. stirringthe mixture was stirred
  3. filtrationThe mixture was filtered through celite
  4. washthe insoluble material was washed with ethyl acetate (100 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-7534b2f8133f4789956522819d92c7ac
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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