Ethyl diazoacetate → Ethyl 3-(4-chlorophenyl)-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylate

HRID 1784043Notes

Reaction equation

HRID 1784043 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[CH:11]=[CH:10][C:9]2=[O:14])=[CH:4][CH:3]=1.[CH2:15]([O:17][C:18](=[O:22])[CH:19]=[N+]=[N-])[CH3:16]>C1(C)C(C)=CC=CC=1>[CH2:15]([O:17][C:18]([CH:19]1[CH:10]2[CH:11]1[C:12](=[O:13])[N:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[C:9]2=[O:14])=[O:22])[CH3:16]

Participants

4

Reactant 2

HCID 12192Ethyl diazoacetateHCID 15400Maleimide, N-(p-chlorophenyl)-

Product 1

HCID 3120146Ethyl 3-(4-chlorophenyl)-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylateYield 35%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 19.4 g (93 mmol) of 1-(4-chloro-phenyl)-pyrrole-2,5-dione in 120 ml of xylene was treated with 19.4 ml (187 mmol) of ethyldiazoacetate and refluxed during 12 hrs. Evaporation of the solvent and chromatography on silica gel with toluene and then a gradient of toluene/AcOEt from 95:5 to 90:10 gave 9.5 g(35%) of the title compound. Off white solid. MS: 294 (M+H)+.

Workup

  1. temperaturerefluxed during 12 hrs
  2. customEvaporation of the solvent and chromatography on silica gel with toluene

Sources & evidence

ORD record
ord-01f24a38bb21480da8e3ab11a692e97a
Source dataset
uspto-grants-2009_03
Patent number
US07501413B2

Reaction notes

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