Hydrochloric Acid → HCID 18423355, compound

HRID 1281901Notes

Reaction equation

HRID 1281901 reaction equation
[C:1]([C:3]1[C:8]([S:9][CH3:10])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].[ClH:11]>CO.[Pd]>[ClH:11].[ClH:11].[NH2:2][CH2:1][C:3]1[C:8]([S:9][CH3:10])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 184233573-(Methylthio)-2-pyridinecarbonitrile

Product 1

HCID 18423355HCID 18423355, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A stirred solution of 659 mg (4.39 mmol) of 2-cyano-3-methylthiopyridine 3-1 in 25 mL of methanol and 5 mL of 6M aq. HCl was hydrogenated over 659 mg of 10% palladium on carbon at 55 psi for 5 h. The catalyst was removed by filtration and the solvents concentrated at reduced pressure. The resulting material was diluted with methanol and concentrated (2×) to give 3-2 as an off-white solid: 1H NMR (CD3OD): δ 2.58 (s, 3H), 4.28 (s, 2H), 7.43 (m, 1H), 7.86 (dd, J 1.3 and 8.1 Hz, 1H), 8.43 (dd, J=1.3 and 4.8 Hz, 1H).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe solvents concentrated at reduced pressure
  3. additionThe resulting material was diluted with methanol
  4. concentrationconcentrated (2×)

Sources & evidence

ORD record
ord-06826d6056e44a4b9785b1140d8905bd
Source dataset
uspto-grants-2002_09
Patent number
US06455532B1

Reaction notes

Loading…