Ethanol → HCID 21479424, compound

HRID 2292712Notes

Reaction equation

HRID 2292712 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[C:5]([N+:11]([O-:13])=[O:12])[CH:4]=1)[CH3:2].C([OH:16])C.[H][H].[OH-].[Na+]>O>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH2:10])=[O:16])=[C:5]([N+:11]([O-:13])=[O:12])[CH:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 21479439HCID 21479439, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21479424HCID 21479424, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2 parts of 4-ethyl-2-nitrobenzenecarbonitrile, 31.6 parts of ethanol, 27.8 parts of hydrogen perioxide (30%) and 1.7 ml of sodium hydroxide 6N was stirred for 1 hour at room temperature. The reaction mixture was diluted with water and the product was extracted with dichloromethane (3×). the combined extracts were washed with water, dried, filtered and evaporated. The residue was crystallized from 2,2'-oxybispropane. The product was filtered off and dried, yielding 1.3 parts (60.9%) of 4-ethyl-2-nitrobenzamide; mp. 175° C. (interim 4).

Workup

  1. extractionthe product was extracted with dichloromethane (3×)
  2. washthe combined extracts were washed with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was crystallized from 2,2'-oxybispropane
  7. filtrationThe product was filtered off
  8. customdried

Sources & evidence

ORD record
ord-b7b15cc91e7b42ec90146221cf4ef6b0
Source dataset
uspto-grants-1997_11
Patent number
US05684049

Reaction notes

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