Ethanol → HCID 16777310, compound

HRID 1717279Notes

Reaction equation

HRID 1717279 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[CH:9][C:3]=1[C:4]([NH:6][CH2:7][CH3:8])=[O:5].[Cl-].[Ca+2].[Cl-].C(O)C>C(OCC)(=O)C.[Fe]>[NH2:13][C:11]1[CH:10]=[CH:9][C:3]([C:4]([NH:6][CH2:7][CH3:8])=[O:5])=[C:2]([Cl:1])[CH:12]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 46473702-Chloro-N-ethyl-4-nitrobenzamideHCID 5284359Calcium Chloride

Product 1

HCID 16777310HCID 16777310, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-N-ethyl-4-nitrobenzamide (2.00 g) obtained in Example 66a), iron powder (2.43 g) and calcium chloride (0.48 g) were suspended in an aqueous solution (30 ml) of 85% ethanol, and the mixture was refluxed for 1 hr. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (100 ml), and the insoluble material was removed by filtration through celite. The filtrate was concentrated, and the residue was purified by silica gel column (ethyl acetate/hexane=1/1 to ethyl acetate) to give the title compound as a yellow powder (1.55 g, 90%).

Workup

  1. temperaturethe mixture was refluxed for 1 hr
  2. customthe insoluble material was removed by filtration through celite
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by silica gel column (ethyl acetate/hexane=1/1 to ethyl acetate)

Sources & evidence

ORD record
ord-46e07da77ed74b37b5ecfe78d598decd
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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