Ammonia → 1-(4-Aminophenyl)-3-azabicyclo[3.1.0]hexane-2,4-dione

HRID 1904789Notes

Reaction equation

HRID 1904789 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]([OH:16])=O)[CH2:10][CH:9]2[C:11](O)=[O:12])=[CH:4][CH:3]=1.[NH3:17]>>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]23[CH2:10][CH:9]2[C:11](=[O:12])[NH:17][C:14]3=[O:16])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 200380431-(4-Aminophenyl)-1,2-cyclopropanedicarboxylic acid

Product 1

HCID 140689341-(4-Aminophenyl)-3-azabicyclo[3.1.0]hexane-2,4-dione

Procedure

In a glass bomb tube, 2.3 g of 1-(4-aminophenyl)-1,2-cyclopropanedicarboxylic acid are stirred in 80 ml of approx. 1N methanolic ammonia solution for 7 days at 100° C. The reaction mixture is evaporated to dryness and the residue is chromatographed over silica gel with hexane/ethyl acetate (4:6). Recrystallisation from ethanol affords white crystals of the title compound, which is identical with the title compound of Example 1.

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. customthe residue is chromatographed over silica gel with hexane/ethyl acetate (4:6)
  3. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-6909bc20c31c4a9f8a89c4819f518c19
Source dataset
uspto-grants-1989_06
Patent number
US04839379

Reaction notes

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