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

HRID 1948579Notes

Reaction equation

HRID 1948579 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 (7-5, 5.1 g, 31.1 mmol) in MeOH (260 mL) was added Pearlman's Catalyst (2.18 g, 3.11 mmol) and concentrated HCl (20.0 mL, 249 mmol). 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 (7-6) 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-1bd4e21eb7fc4e868d3a617c490b4359
Source dataset
uspto-grants-2013_03
Patent number
US08399494B2

Reaction notes

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