Acetate → 2-Methoxy-11-[2-nitroethenyl]-6h-pyrido[2',3':4,5]pyrrolo[2,1-a]-isoindole

HRID 2298756Notes

Reaction equation

HRID 2298756 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]3[CH2:11][C:12]4[C:17]([C:9]3=[C:8]([CH:18]=O)[C:7]=2[N:20]=1)=[CH:16][CH:15]=[CH:14][CH:13]=4.C([O-])(=O)C.[N+:25]([CH3:28])([O-:27])=[O:26]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]3[CH2:11][C:12]4[C:17]([C:9]3=[C:8]([CH:18]=[CH:28][N+:25]([O-:27])=[O:26])[C:7]=2[N:20]=1)=[CH:16][CH:15]=[CH:14][CH:13]=4

Participants

4

Reactant 3

HCID 175AcetateHCID 6375NitromethaneHCID 187582162-Methoxy-6H-pyrido[2',3':4,5]pyrrolo[2,1-a]isoindole-11-carbaldehyde

Product 1

HCID 699693982-Methoxy-11-[2-nitroethenyl]-6h-pyrido[2',3':4,5]pyrrolo[2,1-a]-isoindole

Procedure

600 mg (2.27 mmol) of the compound obtained in Step E dissolved in 25 ml of nitromethane are heated at 120° C. for 3 hours in the presence of 440 mg (5.67 mmol) of animmonium acetate. After returning to room temperature and evaporation to dryness, the reaction mixture is diluted in dichloromethane and washed with water. After drying over magnesium sulphate, evaporation of the organic phase yields the title compound in the form of a yellow solid.

Workup

  1. customAfter returning to room temperature
  2. customevaporation to dryness
  3. additionthe reaction mixture is diluted in dichloromethane
  4. washwashed with water
  5. dry with materialAfter drying over magnesium sulphate, evaporation of the organic phase

Sources & evidence

ORD record
ord-c0a7eb637da84a74a70369c47226d070
Source dataset
uspto-grants-2002_12
Patent number
US06495543B1

Reaction notes

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