8-(4-Nitrophenyl)imidazo[1,2-a]pyridine → Benzenamine,4-imidazo[1,2-a]pyridin-8-yl-

HRID 1982540Notes

Reaction equation

HRID 1982540 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]3[N:12]([CH:16]=[CH:17][N:18]=3)[CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:5]=1)([O-])=O>C(O)(=O)C.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:11]3[N:12]([CH:16]=[CH:17][N:18]=3)[CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 233169598-(4-Nitrophenyl)imidazo[1,2-a]pyridine

Product 1

HCID 13810555Benzenamine,4-imidazo[1,2-a]pyridin-8-yl-

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

Add 45 g of iron powder to a solution of 15 g (62.7 mmol) of the product from Example 19 in 400 ml of 75% acetic acid. Heat to 60°-70° C. for 2 hr. Filter the reaction mixture over celite and concentrate the filtrate to approximately 50 ml under vacuum. Neutralize the residue with saturated sodium carbonate solution and extract with three 200 ml portions of methylene chloride. Dry the combined extracts over sodium sulfate, treat with charcoal and remove the solvent in vacuo. Crystallize the residue from ether to provide the title compound.

Workup

  1. temperatureHeat to 60°-70° C. for 2 hr
  2. filtrationFilter the reaction mixture over celite and
  3. concentrationconcentrate the filtrate to approximately 50 ml under vacuum
  4. extractionNeutralize the residue with saturated sodium carbonate solution and extract with three 200 ml portions of methylene chloride
  5. dry with materialDry the combined extracts over sodium sulfate
  6. additiontreat with charcoal
  7. customremove the solvent in vacuo
  8. customCrystallize the residue from ether

Sources & evidence

ORD record
ord-9129e40b0db1457f91d0a0dff5c0082a
Source dataset
uspto-grants-1986_06
Patent number
US04596872

Reaction notes

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