Ethyl Acetate → (5-(Methylsulfonyl)pyridin-2-yl)methanamine

HRID 559771Notes

Reaction equation

HRID 559771 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[N:12])=[N:9][CH:10]=1)(=[O:4])=[O:3].C(OCC)(=O)C>CO.[Pd]>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][NH2:12])=[N:9][CH:10]=1)(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 591699295-(Methylsulfonyl)pyridine-2-carbonitrile

Product 1

HCID 57354332(5-(Methylsulfonyl)pyridin-2-yl)methanamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 5-methanesulfonyl-pyridine-2-carbonitrile (120 mg, 0.66 mmol) in methanol was hydrogenated over 10% Pd/C catalyst using a continuous flow hydrogenation apparatus (conditions: flow rate 1 mL/minute, 10 bars, 25° C.). The reaction was monitored by HPLC-MS and TLC (ethyl acetate) indicating the disappearance of starting material. The mixture was concentrated in vacuo and then twice diluted with ether-hexanes and concentrated to afford the title compound.

Workup

  1. customa continuous flow hydrogenation apparatus (conditions: flow rate 1 mL/minute, 10 bars, 25° C.)
  2. concentrationThe mixture was concentrated in vacuo
  3. additiontwice diluted with ether-hexanes
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-45ddf36cfbf844c5ac8aa7187db094d8
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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