Methanol → Gentianadine

HRID 1844002Notes

Reaction equation

HRID 1844002 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:9]([C:10]#N)=[CH:8][N:7]=[CH:6][CH:5]=1.CO.C([O-])(O)=[O:15].[Na+]>Cl.C(Cl)(Cl)Cl>[C:10]1(=[O:15])[C:9]2=[CH:8][N:7]=[CH:6][CH:5]=[C:4]2[CH2:3][CH2:2][O:1]1

Participants

6

Reactant 3

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 66803790HCID 66803790, compound

Product 1

HCID 442532GentianadineYield 67.75%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6212ChloroformSolvent

Procedure

4-(2-Hydroxyethyl)nicotinonitrile (I-65b: 1.1 g) in concentrated HCl (30 mL) was refluxed overnight. The reaction was monitored by TLC (10% methanol in CHCl3). The reaction mass was concentrated under reduced pressure and the crude residue was dissolved in water. The resulting reaction mass was basified with saturated NaHCO3 solution and extracted using ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated under reduced pressure to afford 750 mg of the product (67.75% yield).

Workup

  1. concentrationThe reaction mass was concentrated under reduced pressure
  2. dissolutionthe crude residue was dissolved in water
  3. customThe resulting reaction mass
  4. extractionextracted
  5. washThe organic layer was washed with brine solution
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-946a3e8c3b1c4ae4a6b0e9abde2b9fdf
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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