Water → HCID 57387083, compound

HRID 1800569Notes

Reaction equation

HRID 1800569 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-].O.[OH-].[Na+]>C(O)C.[Fe].C(OCC)(=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

8

Reactant 4

HCID 962WaterHCID 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 23925IronCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 2-chloro-3-(1-cyanocyclopropyl)-N-{2-fluoro-5-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide (6.60 g, 14.6 mmol), iron powder (1.68 g, 30 mmol) and calcium chloride (3.33 g, 30 mmol) in ethanol (80 mL)-water (20 mL) was stirred at 80° C. overnight. The reaction mixture was poured into 0.5N aqueous sodium hydroxide solution (500 mL), ethyl acetate (300 mL) was added, the mixture was stirred, and the insoluble material was filtered through celite. The ethyl acetate layer was separated from the filtrate, and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was triturated with diethyl ether to give the title compound (4.23 g, 69%) as a pale-yellow amorphous.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred
  3. filtrationthe insoluble material was filtered through celite
  4. customThe ethyl acetate layer was separated from the filtrate
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe insoluble material was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe obtained residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-8f8f8ac45b224908b8b415921d128e73
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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