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

HRID 1019537Notes

Reaction equation

HRID 1019537 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-pyridinamine

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 preceding stage, and 1 g of Pd/C at 10% in 400 mL of ethanol is stirred vigorously at 20° C. under 5 atm of hydrogen for 4 hours. After this time, the mixture is filtered on a Celite pad and then concentrated at reduced pressure. We thus obtain 9.3 g of the expected product, which is used as it is in the rest of the synthesis.

Workup

  1. filtrationAfter this time, the mixture is filtered on a Celite pad
  2. concentrationconcentrated at reduced pressure
  3. customis in the rest of the synthesis

Sources & evidence

ORD record
ord-d2061bfb8e8542d68ce8f931229ae8c4
Source dataset
uspto-grants-2014_05
Patent number
US08716272B2

Reaction notes

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