Water → HCID 68417577, compound

HRID 1800582Notes

Reaction equation

HRID 1800582 reaction equation
[Cl:1][C:2]1[C:28]([C:29]2([C:32]#[N:33])[CH2:31][CH2:30]2)=[CH:27][CH:26]=[CH:25][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)[C:10]([F:23])=[CH:9][C:8]=1[F:24])=[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[C:10]([F:23])=[CH:9][C:8]([F:24])=[C:7]([NH:6][C:4](=[O:5])[C:3]3[CH:25]=[CH:26][CH:27]=[C:28]([C:29]4([C:32]#[N:33])[CH2:30][CH2:31]4)[C:2]=3[Cl:1])[CH:12]=2)=[N:15][CH:16]=1

Participants

8

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 5284359Calcium ChlorideHCID 68417567HCID 68417567, compound

Product 1

HCID 68417577HCID 68417577, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixed solution of 2-chloro-3-(1-cyanocyclopropyl)-N-{2,4-difluoro-5-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide (5.20 g, 11 mmol), iron powder (1.24 g, 22 mmol) and calcium chloride (2.45 g, 22 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 (4.25 g, 88%) as a pale-yellow amorphous.

Workup

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

Sources & evidence

ORD record
ord-026ead8f69a04c39821f3ac31858e414
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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