Hydrogen Peroxide → HCID 89815261, compound

HRID 1487154Notes

Reaction equation

HRID 1487154 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2([C:13]#[N:14])[CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[OH-:15].[K+].OO>CC(O)C.[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2([C:13]([NH2:14])=[O:15])[CH2:11][CH2:12]2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14797Potassium HydroxideHCID 20026167HCID 20026167, compound

Product 1

HCID 89815261HCID 89815261, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-(3-nitrophenyl)cyclopropanecarbonitrile (1.6 g, 8.50 mmol) in 2-Propanol (50 ml) was added triethylbenzylammonium chloride (0.058 g, 0.255 mmol) and 25% aq KOH solution (5 ml). Resulting solution was stirred for 5 min. and H2O2 (10 ml, 98 mmol, ca. 30% solution in water) was added. Reaction mixture was heated at 50° C. for 4 h. Solvent was evaporated in vacuo and residue was suspended in water (200 ml). Precipitate was filtered and dried to obtain 1-(3-nitrophenyl)cyclopropane carboxamide (1.104 g, 5.36 mmol, 63% yield).

Workup

  1. customReaction mixture
  2. customSolvent was evaporated in vacuo and residue
  3. filtrationPrecipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-1a7a9b5409c34e4aafc01d8d7c680739
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

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