2-Amino-5-nitropyridine → HCID 67273481, compound

HRID 600622Notes

Reaction equation

HRID 600622 reaction equation
Br[CH2:2][C:3](=O)[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=1>C1COCC1.C(O)C>[N+:20]([C:17]1[CH:18]=[CH:19][C:14]2[N:15]([CH:2]=[C:3]([C:4]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)=[O:5])[N:13]=2)[CH:16]=1)([O-:22])=[O:21]

Participants

5

Reactant 2

HCID 778882-Amino-5-nitropyridineHCID 125689113-Bromo-1-phenylpropane-1,2-dione

Product 1

HCID 67273481HCID 67273481, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of 0.48 g of 3-bromo-1-phenylpropane-1,2-dione in a mixture of 3 mL of THF and 0.5 mL of ethanol is added 0.25 g of 2-amino-5-nitropyridine. The reaction mixture is heated for 15 minutes at 160° C. in a microwave machine. The solid formed is separated out, taken up in 3 mL of ethanol and refluxed for 6 hours. After evaporating off the solvent, the residue is taken up in ethyl acetate and diluted with sodium hydroxide solution. The organic phase is washed with water, dried and then evaporated to give 0.42 g of (6-nitroimidazo[1,2-a]pyridin-2-yl)(phenyl)methanone in the form of a brown solid, which is used without further purification.

Workup

  1. customThe solid formed
  2. customis separated out
  3. temperaturerefluxed for 6 hours
  4. customAfter evaporating off the solvent
  5. additiondiluted with sodium hydroxide solution
  6. washThe organic phase is washed with water
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-f68d61f29edf4a5db764361f4214abe6
Source dataset
uspto-grants-2011_03
Patent number
US07902219B2

Reaction notes

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