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

HRID 1767554Notes

Reaction equation

HRID 1767554 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:14]3[C:9]([CH2:10][CH2:11][CH2:12][CH2:13]3)=[C:8]([CH:15]=O)[C:7]=2[N:17]=1.C([O-])(=O)C.[NH4+].[N+:23]([CH3:26])([O-:25])=[O:24]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:14]3[C:9]([CH2:10][CH2:11][CH2:12][CH2:13]3)=[C:8]([CH:15]=[CH:26][N+:23]([O-:25])=[O:24])[C:7]=2[N:17]=1

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 112532192-Methoxy-6,7,8,9-tetrahydropyrido[2,3-b]indolizine-10-carbaldehyde

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-a4b6a2aaa17344808e2825c74cd29499
Source dataset
uspto-grants-2007_06
Patent number
US07235550B2

Reaction notes

Loading…