Hydrochloric Acid → HCID 58294639, compound

HRID 521014Notes

Reaction equation

HRID 521014 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7](=O)[C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[CH:10][N:9]=3.Cl>[Pd].O=[Pt]=O.CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C@H:8]3[C@@H:13]([C:14]=2[CH:15]=1)[CH2:12][CH2:11][CH2:10][NH:9]3

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 58294438HCID 58294438, compound

Product 1

HCID 58294639HCID 58294639, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A mixture of 6-methoxy-indeno[2,1-b]pyridin-9-one (2.00 g), 10% palladium on carbon (0.30 g), 4 M aqueous hydrochloric acid (6 mL), and methanol (100 mL) is shaken under hydrogen atmosphere (3 bar) at room temperature for 4 h. PtO2 (0.20 g) is then added and shaking is continued under hydrogen atmosphere (1 bar) at room temperature for another 36 h. The catalysts are separated by filtration and the filtrate is concentrated. The residue is basified by the addition of 2 M aqueous NaOH solution and the resulting mixture is extracted with ethyl acetate. The combined extracts are washed with brine, dried (Na2SO4), and the solvent is evaporated. The residue is chromatographed on silica gel (dichloromethane/methanol containing 1% NH3 90:10→75:25) to give the title compound as a colorless oil. Yield: 1.00 g (52% of theory); LC (method 1): tR=1.50 min; Mass spectrum (ESI+): m/z=204 [m+H]+.

Workup

  1. stirringshaking
  2. customat room temperature
  3. customfor another 36 h
  4. customThe catalysts are separated by filtration
  5. concentrationthe filtrate is concentrated
  6. additionThe residue is basified by the addition of 2 M aqueous NaOH solution
  7. extractionthe resulting mixture is extracted with ethyl acetate
  8. washThe combined extracts are washed with brine
  9. dry with materialdried (Na2SO4)
  10. customthe solvent is evaporated
  11. customThe residue is chromatographed on silica gel (dichloromethane/methanol containing 1% NH3 90:10→75:25)

Sources & evidence

ORD record
ord-b8d51b79532e43efbace0f38671a338f
Source dataset
uspto-grants-2016_05
Patent number
US09328072B2

Reaction notes

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