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

HRID 1904791Notes

Reaction equation

HRID 1904791 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.[CH3:17][NH2:18]>CO>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]23[CH2:10][CH:9]2[C:11](=[O:12])[N:18]([CH3:17])[C:14]3=[O:16])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 200380431-(4-Aminophenyl)-1,2-cyclopropanedicarboxylic acid

Product 1

HCID 101713541-(4-Aminophenyl)-3-methyl-3-azabicyclo[3.1.0]hexane-2,4-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 220 mg of 1-(4-aminophenyl)-1,2-cyclopropanedicarboxylic acid, 10 ml of methanol and 0.26 ml of methylamine (40%) is stirred in a glass bomb tube for 7 days at 100° C. The mixture is concentrated in vacuo and the residue is chromatographed over a column of silica gel with a 4:6 mixture of hexane/ethyl acetate. Recrystallisation from ethyl acetate/petroleum ether affords yellow crystals of the title compound, which is identical with the title compound of Example 3(a).

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. customthe residue is chromatographed over a column of silica gel with a 4:6 mixture of hexane/ethyl acetate
  3. customRecrystallisation from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-ec7618d420f1443a8b83f38bce7036c1
Source dataset
uspto-grants-1989_06
Patent number
US04839379

Reaction notes

Loading…