1-(6-Nitro-pyridin-3-yl)-azetidin-3-ol → 1-(6-Aminopyridin-3-yl)azetidin-3-ol

HRID 407770Notes

Reaction equation

HRID 407770 reaction equation
[N+:1]([C:4]1[N:9]=[CH:8][C:7]([N:10]2[CH2:13][CH:12]([OH:14])[CH2:11]2)=[CH:6][CH:5]=1)([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[N:9]=[CH:8][C:7]([N:10]2[CH2:11][CH:12]([OH:14])[CH2:13]2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 592909581-(6-Nitro-pyridin-3-yl)-azetidin-3-ol

Product 1

HCID 580438121-(6-Aminopyridin-3-yl)azetidin-3-olYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A 100-mL single-neck round-bottomed flask was purged with nitrogen and charged with 147a (1.0 g, 5.1 mmol), 10% palladium on carbon (10% wet, 100 mg), and ethanol (40 mL). The mixture was evacuated, charged with hydrogen gas, and stirred at room temperature for 5 h. The hydrogen was then evacuated and nitrogen was charged into the flask. The catalyst was removed by filtration through a pad of CELITE® and the filtrate was concentrated under reduced pressure to afford 147b as a yellow solid (792 mg, 85%). MS-ESI: [M+H]+ 166.1.

Workup

  1. customA 100-mL single-neck round-bottomed flask was purged with nitrogen
  2. customThe mixture was evacuated
  3. additioncharged with hydrogen gas
  4. customThe hydrogen was then evacuated
  5. additionnitrogen was charged into the flask
  6. customThe catalyst was removed by filtration through a pad of CELITE®
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1629b33d2f28403fa7d2d6bb66d1a26b
Source dataset
uspto-grants-2014_06
Patent number
US08754077B2

Reaction notes

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