Hydrochloric Acid → 1-(5,6-Dimethoxypyridin-2-yl)methanamine

HRID 1802347Notes

Reaction equation

HRID 1802347 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[C:5]([C:11]#[N:12])[N:4]=1.Cl>CO.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[C:5]([CH2:11][NH2:12])[N:4]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 467367605,6-Dimethoxypicolinonitrile

Product 1

HCID 574847121-(5,6-Dimethoxypyridin-2-yl)methanamine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2,3-dimethoxy-6-cyanopyridine (5-5, 5.1 g, 31.1 mmol) in MeOH (260 mL) was added Pearlman's catalyst (2.18 g, 3.11 mmol, 20 weight percent) and concentrated HCl (20.0 mL, 249 mmol, 12M). The system was then stirred under an atmosphere of hydrogen via a balloon for 1.5 h. The reaction contents were filtered through a pad of celite and methanol was removed in vacuo. The crude mixture was then basified using saturated Na2CO3 and then extracted using 4:1 Chloroform:Ethanol. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated to yield the desired product (5-6) as a bone semi-solid. ESI+MS [M+H]+ C8H12N2O2: M-16 (—NH2), 152.06 found, 152.2 required.

Workup

  1. customThe reaction contents
  2. filtrationwere filtered through a pad of celite and methanol
  3. customwas removed in vacuo
  4. extractionextracted
  5. washThe organic phase was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-01cd8546ad8f496083cc1426bb9d113a
Source dataset
uspto-grants-2013_01
Patent number
US08349872B2

Reaction notes

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