Hydrochloric Acid → (5,6-Dimethoxypyridin-3-yl)methanamine

HRID 1802335Notes

Reaction equation

HRID 1802335 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:11][CH3:12])=[N:5][CH:6]=[C:7]([CH:10]=1)[C:8]#[N:9].Cl>CO.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3]1[CH:10]=[C:7]([CH2:8][NH2:9])[CH:6]=[N:5][C:4]=1[O:11][CH3:12]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 467367595,6-Dimethoxypyridine-3-carbonitrile

Product 1

HCID 59187381(5,6-Dimethoxypyridin-3-yl)methanamine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5,6-dimethoxynicotinonitrile (1-3, 0.600 g, 3.65 mmol, 1.0 equiv) in methanol (20 mL) under a nitrogen atmosphere was added Pearlman's catalyst (0.205 g, 0.292 mmol, 0.08 equiv, 20 weight percent) and concentrated HCl (2.44 mL), and the reaction was place under an atmosphere of hydrogen. After 2 h, the reaction was placed under an atmosphere of nitrogen and filtered through celite to remove the catalyst. The reaction mixture was dissolved in EtOAc, dried over MgSO4 and concentrated to an oily solid (1-4) of high purity. ESI+MS [M+H]+ C8H12N2O2 calc'd 169.1. found 169.1.

Workup

  1. filtrationfiltered through celite
  2. customto remove the catalyst
  3. dissolutionThe reaction mixture was dissolved in EtOAc
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to an oily solid (1-4) of high purity

Sources & evidence

ORD record
ord-7b815ca95cbe4295815bd8a10047e0b5
Source dataset
uspto-grants-2013_01
Patent number
US08349872B2

Reaction notes

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