Ethanol → HCID 21084114, compound

HRID 347835Notes

Reaction equation

HRID 347835 reaction equation
[Br:1][C:2]1[N:7]2[N:8]=[C:9]([CH3:14])[C:10]([N+:11]([O-])=O)=[C:6]2[CH:5]=[CH:4][CH:3]=1.C(O)C.O>[Zn].C(O)(=O)C>[Br:1][C:2]1[N:7]2[N:8]=[C:9]([CH3:14])[C:10]([NH2:11])=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 962WaterHCID 21084113HCID 21084113, compound

Product 1

HCID 21084114HCID 21084114, compoundYield 47.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a Suspension of 7-bromo-2-methyl-3-nitropyrazolo[1,5-a]pyridine (890 mg) in a mixed solution of ethanol (20 mL), water (10 mL) and acetic acid (2 mL) was added zinc powder (890 mg) at room temperature, and the reaction mixture was heated and stirred for 30 minutes at 60° C. After filtering off the insoluble residue, the filtrate was extracted with ethyl acetate and the organic extract was washed with saturated aqueous sodium bicarbonate and brine. The obtained organic extract was dried over anhydrous magnesium sulfate and filtered, the solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography and [7-bromo-2-methylpyrazolo[1,5-a]pyridin-3-yl]amine (371 mg) was obtained as an brown oil from the n-hexane:ethyl acetate (1:1) fraction.

Workup

  1. temperaturethe reaction mixture was heated
  2. filtrationAfter filtering off the insoluble residue
  3. extractionthe filtrate was extracted with ethyl acetate
  4. extractionthe organic extract
  5. washwas washed with saturated aqueous sodium bicarbonate and brine
  6. extractionThe obtained organic extract
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent was evaporated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b9ac6041c5714bca8612f7a895781052
Source dataset
uspto-grants-2007_02
Patent number
US07176216B2

Reaction notes

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