Water → N-[3-(4-aminophenoxy)-4-methoxyphenyl]-3-(1-cyanocyclopropyl)benzamide

HRID 2190404Notes

Reaction equation

HRID 2190404 reaction equation
[C:1]([C:3]1([C:6]2[CH:7]=[C:8]([CH:30]=[CH:31][CH:32]=2)[C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=3)[CH:13]=2)=[O:10])[CH2:5][CH2:4]1)#[N:2].[Cl-].[Ca+2].[Cl-].O.[OH-].[Na+]>C(O)C.C(OCC)(=O)C>[NH2:27][C:24]1[CH:23]=[CH:22][C:21]([O:20][C:14]2[CH:13]=[C:12]([NH:11][C:9](=[O:10])[C:8]3[CH:30]=[CH:31][CH:32]=[C:6]([C:3]4([C:1]#[N:2])[CH2:5][CH2:4]4)[CH:7]=3)[CH:17]=[CH:16][C:15]=2[O:18][CH3:19])=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 5284359Calcium ChlorideHCID 673136633-(1-cyanocyclopropyl)-N-[4-methoxy-3-(4-nitrophenoxy)phenyl]benzamide

Product 1

HCID 67311871N-[3-(4-aminophenoxy)-4-methoxyphenyl]-3-(1-cyanocyclopropyl)benzamideYield 89.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(1-cyanocyclopropyl)-N-[4-methoxy-3-(4-nitrophenoxy)phenyl]benzamide (2.10 g, 4.89 mmol), reduced iron (0.56 g, 10.0 mmol) and calcium chloride (1.11 g, 10.0 mmol) in ethanol (40 mL)/water (10 mL) was stirred at 80° C. for 18 hr. The reaction mixture was poured into 0.5N aqueous sodium hydroxide solution (400 mL), ethyl acetate (300 mL) was added and the mixture was stirred. The insoluble material was filtered off through celite, and the organic layer was separated and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane/ethyl acetate=1:1), and triturated with diethyl ether to give the title compound (1.74 g, 82%) as a pale-yellow solid.

Workup

  1. additionwas added
  2. filtrationThe insoluble material was filtered off through celite
  3. customthe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent:hexane/ethyl acetate=1:1)
  7. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-81efbccf334746b4beb8b2dc9e061a98
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

Loading…