Methane → HCID 58938610, compound

HRID 598107Notes

Reaction equation

HRID 598107 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:6](=[O:22])[N:7]2[C:12]=1[CH:11]=[CH:10][CH:9]=[C:8]2[C:13]1[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=1[CH3:21])#[N:2].Cl.[CH4:29].[CH:30](=O)[CH2:31][CH3:32].C(O[BH-](O[C:44](=O)[CH3:45])OC(=O)C)(=O)C.[Na+]>C(O)C.ClCCCl.[OH-].[OH-].[Pd+2]>[CH2:30]([N:2]([CH2:1][C:3]1[CH:4]=[C:5]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:6](=[O:22])[N:7]2[C:12]=1[CH:11]=[CH:10][CH:9]=[C:8]2[C:13]1[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=1[CH3:21])[CH2:29][CH2:44][CH3:45])[CH2:31][CH3:32]

Participants

9

Reactant 5

HCID 297MethaneHCID 313Hydrochloric AcidHCID 527PropanalHCID 5049666Sodium triacetoxyborohydrideHCID 86613888HCID 86613888, compound

Product 1

HCID 58938610HCID 58938610, compoundYield 43.8%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 111,2-DichloroethaneSolventHCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

Ethyl 1-cyano-6-mesityl-4-oxo-4H-quinolizine-3-carboxylate (0.110 g, 0.30 mmol) was dissolved in 20 mL ethanol and HCl (0.15 mL) and treated with 20% Pd(OH)2 over charcoal (0.050 g). The solution was evacuated and filled with a hydrogen balloon. After 5 h, the solution was filtered and concentrated to give a yellow solid. The hydrochloride salt was then dissolved in 1,2-dichloroethane (5 mL) and propionaldehyde (0.078 mL, 1.1 mmol) was added followed by sodium triacetoxyborohydride (0.23 g, 1.1 mmol). The reaction was heated to 40° C. overnight. The solution was cooled, quenched with water. Extraction with ethyl acetate was followed by drying the organic layer, concentration, and flash chromatography (ethyl acetate) to give 0.059 g (42% yield) of the title compound.

Workup

  1. customThe solution was evacuated
  2. additionfilled with a hydrogen balloon
  3. filtrationthe solution was filtered
  4. concentrationconcentrated
  5. customto give a yellow solid
  6. temperatureThe solution was cooled
  7. customquenched with water
  8. extractionExtraction with ethyl acetate
  9. customby drying
  10. concentrationthe organic layer, concentration, and flash chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-1405864542a34fd3bbac78fbebfdf548
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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