Hydrochloric Acid → HCID 89535359, compound

HRID 595047Notes

Reaction equation

HRID 595047 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:13])[C:6]([C:11]#[N:12])=[N:7][C:8]=1[O:9][CH3:10].Cl>CO.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:13])[C:6]([CH2:11][NH2:12])=[N:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 895353615,6-Dimethoxy-3-methyl-2-pyridinecarbonitrile

Product 1

HCID 89535359HCID 89535359, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5,6-dimethoxy-3-methylpyridine-2-carbonitrile (1-6e, 577 mg, 3.24 mmol) in MeOH (27 mL) was added Pearlman's catalyst (455 mg, 0.648 mmol, 20 weight percent) and concentrated HCl (2.13 mL, 25.9 mmol, 12M). The system was then stirred under an atmosphere of hydrogen (45 psi) overnight. 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 a crude product which was purified through column chromatography (SiO2, 0-12% MeOH (containing 10% NH4OH) in dichlormethane) to give the desired product (1-6) as a yellow oil. ESI+ MS [M+H]+ C9H15N2O2: M−16 (—NH2)=167.3.

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
  9. customto yield a crude product which
  10. customwas purified through column chromatography (SiO2, 0-12% MeOH (containing 10% NH4OH) in dichlormethane)

Sources & evidence

ORD record
ord-72274e5df4644b12b53b76dca03b049b
Source dataset
uspto-grants-2016_01
Patent number
US09242995B2

Reaction notes

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