2-(Azetidin-1-yl)-5-nitropyridine → 6-(1-Azetidinyl)-3-pyridinamine

HRID 1948778Notes

Reaction equation

HRID 1948778 reaction equation
[N:1]1([C:5]2[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][N:6]=2)[CH2:4][CH2:3][CH2:2]1.[H][H]>C(O)C.[Pd]>[NH2:11][C:8]1[CH:7]=[N:6][C:5]([N:1]2[CH2:4][CH2:3][CH2:2]2)=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 668504742-(Azetidin-1-yl)-5-nitropyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 552816836-(1-Azetidinyl)-3-pyridinamineYield 97.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 11.5 g (64.18 mmol) of 2-(azetidin-1-yl)-5-nitropyridine, prepared in the previous stage, and of 1 g of Pd/C at 10% in 400 ml of ethanol is stirred vigorously at 20° C. under 5 atmospheres of hydrogen for 4 hours. After this period of time, the mixture is filtered through a celite buffer and then concentrated under reduced pressure. 9.3 g of the expected product are thus obtained, which product is used as it is in the subsequent synthesis.

Workup

  1. customprepared in the previous stage
  2. waitAfter this period of time
  3. filtrationthe mixture is filtered through a celite buffer and
  4. concentrationthen concentrated under reduced pressure

Sources & evidence

ORD record
ord-a25b34cb36814bfab91c1771c42e3ac4
Source dataset
uspto-grants-2013_03
Patent number
US08399491B2

Reaction notes

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