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

HRID 1904796Notes

Reaction equation

HRID 1904796 reaction equation
[N+:1](=[CH2:3])=[N-].[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]23[CH2:16][CH:15]2[C:14](=[O:17])N[C:12]3=[O:18])=[CH:7][CH:6]=1>CO>[NH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]23[CH2:16][CH:15]2[C:14](=[O:17])[N:1]([CH3:3])[C:12]3=[O:18])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 140689341-(4-Aminophenyl)-3-azabicyclo[3.1.0]hexane-2,4-dione

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An approx. 0.3 molar solution of diazomethane is added dropwise at 0° C. to a solution of 202 mg of 1-(4-aminophenyl)-3-azabicyclo[3.1.0]hexane-2,4-dione in 10 ml of methanol. The reaction mixture is allowed to stand for 16 hours, concentrated, and partitioned twice between ethyl acetate and water. The organic phases are dried over magnesium sulfate, filtered and concentrated. The residue is crystallised from ethyl acetate/petroleum ether, affording the title compound which is identical with the title compound of Example 3(a).

Workup

  1. concentrationconcentrated
  2. custompartitioned twice between ethyl acetate and water
  3. dry with materialThe organic phases are dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is crystallised from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-2dc5d8f9ce894ff3b234158bdef31a88
Source dataset
uspto-grants-1989_06
Patent number
US04839379

Reaction notes

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