Nitromethane → 7-[(E)-2-nitroethenyl]-2,3-dihydro-1H-imidazo[1,2-b]pyrazole-1-carbaldehyde

HRID 349569Notes

Reaction equation

HRID 349569 reaction equation
[N:1]1([CH:11]=[O:12])[C:8]2[N:4]([N:5]=[CH:6][C:7]=2[CH:9]=O)[CH2:3][CH2:2]1.C([O-])(=O)C.[NH4+].[N+:18]([CH3:21])([O-:20])=[O:19]>>[N+:18](/[CH:21]=[CH:9]/[C:7]1[CH:6]=[N:5][N:4]2[CH2:3][CH2:2][N:1]([CH:11]=[O:12])[C:8]=12)([O-:20])=[O:19]

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 179619742,3-dihydro-1H-imidazo[1,2-b]pyrazole-1,7-dicarbaldehyde

Product 1

HCID 179619667-[(E)-2-nitroethenyl]-2,3-dihydro-1H-imidazo[1,2-b]pyrazole-1-carbaldehyde

Procedure

A solution of 2,3-dihydro-1H-imidazo[1,2-b]pyrazole-1,7-dicarbaldehyde (1 g) and ammonium acetate (653 mg) in nitromethane (20 ml) was refluxed for 4 hours. The reaction mixture was evaporated under reduced pressure and extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give 7-[(E)-2-nitroethenyl]-2,3-dihydro-1H-imidazo[1,2-b]pyrazole-1-carbaldehyde (1.00 g).

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. extractionextracted with dichloromethane
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9a07fa69d9b646a68acadc19aaa67ca9
Source dataset
uspto-grants-2007_02
Patent number
US07179801B2

Reaction notes

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