Nitric Acid → 3-Acetyl-1-(p-nitrophenyl)-3-azabicyclo[3.1.0]hexane

HRID 371947Notes

Reaction equation

HRID 371947 reaction equation
[C:1]([N:4]1[CH2:9][CH:8]2[C:6]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)([CH2:7]2)[CH2:5]1)(=[O:3])[CH3:2].[N+:16]([O-])([OH:18])=[O:17]>S(=O)(=O)(O)O>[C:1]([N:4]1[CH2:9][CH:8]2[C:6]([C:10]3[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=3)([CH2:7]2)[CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 128913713-Acetyl-1-phenyl-3-azabicyclo[3.1.0]hexane

Product 1

HCID 203522533-Acetyl-1-(p-nitrophenyl)-3-azabicyclo[3.1.0]hexane

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a suspension of 3-acetyl-1-phenyl-3-azabicyclo[3.1.0]hexane in concentrated sulfuric acid is added concentrated nitric acid during 15 minutes at 0°-10° C. The resulting mixture is stirred at room temperature for 15 minutes and then poured onto ice. The product, 3-acetyl-1-(p-nitrophenyl)-3-azabicyclo[3.1.0]hexane, is collected by filtration.

Workup

  1. additionpoured onto ice
  2. filtrationThe product, 3-acetyl-1-(p-nitrophenyl)-3-azabicyclo[3.1.0]hexane, is collected by filtration

Sources & evidence

ORD record
ord-d1b9fad4d8e34d0085c93e1a21f63a0a
Source dataset
uspto-grants-1978_05
Patent number
US04088652

Reaction notes

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