Nitromethane → 2-Methoxy-10-[2-nitroethenyl]-6,7,8,9-tetrahydropyrido[2,3-b]indolizine

HRID 433064Notes

Reaction equation

HRID 433064 reaction equation
BrC1C=C[CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[N:9][C:10]([O:14][CH3:15])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1.[C:20]([O-])(=O)[CH3:21].[NH4+].[N+:25](C)([O-:27])=[O:26]>>[CH3:15][O:14][C:10]1[CH:11]=[CH:12][C:13]2[N:5]3[C:6]([CH2:17][CH2:16][CH2:3][CH2:4]3)=[C:7]([CH:21]=[CH:20][N+:25]([O-:27])=[O:26])[C:8]=2[N:9]=1

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 178207361-(2-Bromobenzyl)-5-methoxy-1H-pyrrolo[3,2-b]pyridine

Product 1

HCID 694179332-Methoxy-10-[2-nitroethenyl]-6,7,8,9-tetrahydropyrido[2,3-b]indolizine

Procedure

550 mg (2.39 mmol) of the compound obtained in Step C dissolved in 25 ml of nitromethane are heated at 120° C., for 3 hours in the presence of 460 mg (5.97 mmol) of ammonium acetate. After returning to room temperature and evaporation to dryness, the reaction mixture is diluted in dichloromethane and washed with water. The organic phase is dried over magnesium sulphate, filtered and evaporated. After washing with a pentane/diethyl ether mixture, the title compound is obtained in the form of a brown 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 materialThe organic phase is dried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. washAfter washing with a pentane/diethyl ether mixture

Sources & evidence

ORD record
ord-3bb2254a253443448573f0153302b909
Source dataset
uspto-grants-2003_12
Patent number
US06667304B2

Reaction notes

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