Ethylamine → 6-(2-Nitro-1-propenyl)imidazo[1,2-a]pyridine

HRID 414332

Reaction equation

HRID 414332 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[C:8]([CH:10]=O)[CH:7]=[CH:6][C:5]=12.[N+:12]([CH2:15][CH3:16])([O-:14])=[O:13].C(N)C>C(O)C.C(N)CCC>[N+:12]([C:15]([CH3:16])=[CH:10][C:8]1[CH:7]=[CH:6][C:5]2[N:4]([CH:3]=[CH:2][N:1]=2)[CH:9]=1)([O-:14])=[O:13]

Participants

6

Reactant 3

HCID 6341EthylamineHCID 6587NitroethaneHCID 7164582Imidazo[1,2-a]pyridine-6-carbaldehyde

Product 1

HCID 539155686-(2-Nitro-1-propenyl)imidazo[1,2-a]pyridineYield 11.9%

Reagents, catalysts & solvents 2

HCID 8007ButylamineCatalystHCID 702EthanolSolvent

Procedure

In 40 ml of ethanol, 6.9 g of 6-imidazo[1,2-a]pyridinecarbaldehyde was stirred under reflux for 14 hours, together with 10.6 g of nitroethane and 30 drops of n-butyl amine. Then, a small quantity of ethyl amine was added thereto and the mixture was stirred under reflux for further 18 hours. After insoluble matter was removed by filtration upon heating, 50 ml of ethanol and 150 ml of ether were further added to remove insoluble matter by filtration. The solvent was removed by distillation under reduced pressure and the residue was recrystallized twice from ethanol to obtain 1.14 g of 6-(2-nitro-1-propenyl)imidazo[1,2-a]pyridine.

Workup

  1. temperatureunder reflux for further 18 hours
  2. customAfter insoluble matter was removed by filtration
  3. temperatureupon heating
  4. addition50 ml of ethanol and 150 ml of ether were further added
  5. customto remove insoluble matter
  6. filtrationby filtration
  7. customThe solvent was removed by distillation under reduced pressure
  8. customthe residue was recrystallized twice from ethanol

Sources & evidence

ORD record
ord-57882014ec2d410fa092ab3358781700
Source dataset
uspto-grants-1988_12
Patent number
US04791203

Linked notes

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