Hydrochloric Acid → HCID 16228735, compound

HRID 974796Notes

Reaction equation

HRID 974796 reaction equation
[N+:1]([C:4]1[C:5]([N:10]2[CH:14]=[CH:13][CH:12]=[N:11]2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O.Cl[Sn]Cl.O.Cl>C(O)C>[NH2:1][C:4]1[C:5]([N:10]2[CH:14]=[CH:13][CH:12]=[N:11]2)=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2755764HCID 2755764, compoundHCID 43835034Tin dichloride dihydrate

Product 1

HCID 16228735HCID 16228735, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 3-nitro-2-(pyrazol-1-yl) pyridine (670 mg, 3.72 mmol) in ethanol (10 mL) was added a 1M solution of SnCl2.H2O in 6N aqueous HCl (14.5 mL, 14.5 mmol). The mixture was heated at reflux for 10 min, and the solvent was removed with a rotary evaporator. 10% aqueous sodium hydroxide solution was added until most of the material dissolved, and the mixture was extracted with dichloromethane. The organic extracts were dried over sodium sulfate and concentrated to afford 376 mg (68%) of 3-amino-2-(pyrazol-1-yl) pyridine as a brown oil. 1H NMR (CDCl3) δ5.62 (br s, 2 ), 6.46 (m, 1), 7.05 (dd, 1, J=5, 8), 7.24 (dd, 1, J=2, 8), 7.74 (m, 1), 7.85 (dd, 1, J=2, 5), 8.54 (d, 1, J=3).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 10 min
  3. customthe solvent was removed with a rotary evaporator
  4. addition10% aqueous sodium hydroxide solution was added until most of the material
  5. dissolutiondissolved
  6. extractionthe mixture was extracted with dichloromethane
  7. dry with materialThe organic extracts were dried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-606103c60fc34533bef1b8a226d4c4ba
Source dataset
uspto-grants-1997_03
Patent number
US05607926

Reaction notes

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