HCID 178526787, compound → HCID 178508009, compound

HRID 506586Notes

Reaction equation

HRID 506586 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:10][C:7]2=[N:8][CH:9]=1)([O-])=O>C(O)(=O)C.[Fe]>[C:13]1([C:11]2[NH:10][C:7]3=[N:8][CH:9]=[C:4]([NH2:1])[CH:5]=[C:6]3[N:12]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 1

HCID 178526787HCID 178526787, compound

Product 1

HCID 178508009HCID 178508009, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

12.0 g 6-nitro-2-phenyl-3H-imidazo[4,5-b]pyridine were dissolved in 1 l acetic acid. 18 g iron powder were added and the mixture heated to 80° C. with stirring. After 2 hrs the mixture was cooled to room temperature and filtered over Celite. The celite pad was washed with methanol and the combined filtrates were evaporated. The residue was dissolved methanol/dichloromethane 1:1 and filtered over silica. The filtrate was concentrated to a volume of 100 ml, the resulting precipitate collected by filtration and washed with methanol.

Workup

  1. temperatureAfter 2 hrs the mixture was cooled to room temperature
  2. filtrationfiltered over Celite
  3. washThe celite pad was washed with methanol
  4. customthe combined filtrates were evaporated
  5. dissolutionThe residue was dissolved methanol/dichloromethane 1:1
  6. filtrationfiltered over silica
  7. concentrationThe filtrate was concentrated to a volume of 100 ml
  8. filtrationthe resulting precipitate collected by filtration
  9. washwashed with methanol

Sources & evidence

ORD record
ord-7eccfa8a6b064489a8be3fe27790677f
Source dataset
uspto-grants-2010_08
Patent number
US07786113B2

Reaction notes

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