HCID 21413766, compound → Phenanthridine, 1,2,3,4,7,8,9,10-octahydro-

HRID 2071410Notes

Reaction equation

HRID 2071410 reaction equation
Cl.[CH:2]1[C:15]2[C:6](=[N:7][CH:8]=[C:9]3[C:14]=2[CH2:13][CH2:12][CH2:11][CH2:10]3)[CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.O.[H][H].[Pt]=O>[CH2:2]1[C:15]2[C:6](=[N:7][CH:8]=[C:9]3[C:14]=2[CH2:13][CH2:12][CH2:11][CH2:10]3)[CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 1

HCID 21413766HCID 21413766, compound

Product 1

HCID 641096Phenanthridine, 1,2,3,4,7,8,9,10-octahydro-Yield 100.6%

Reagents, catalysts & solvents 4

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 178418361HCID 178418361, compoundSolvent2×

Procedure

7,8,9,10-Tetrahydrophenanthridine hydrochloride (29 g, 0.13 mole) was dissolved in a mixture of glacial acetic acid (200 ml.) and water (10 ml.) and hydrogenated at 50 psi of hydrogen and room temperature over platinum oxide (750 mg.) until the theoretical uptake of hydrogen (0.26 mole) was observed. The solution was filtered and the solvents removed under reduced pressure. The residue was dissolved in water (100 ml.), and pH adjusted to 9 with Na2CO3 and the solution extracted with diethyl ether (3 × 100 ml.). Drying (MgSO4) and evaporation of the combined organic layers gave a colourless oil, distillation of which gave the title compound (24.5 g, 99%) Bpt 110°-2° C./0.05 mm

Workup

  1. filtrationThe solution was filtered
  2. customthe solvents removed under reduced pressure
  3. dissolutionThe residue was dissolved in water (100 ml.)
  4. extractionthe solution extracted with diethyl ether (3 × 100 ml.)
  5. customDrying
  6. custom(MgSO4) and evaporation of the combined organic layers
  7. customgave
  8. distillationa colourless oil, distillation of which

Sources & evidence

ORD record
ord-036b889854a14018b2125dc04ede175a
Source dataset
uspto-grants-1977_09
Patent number
US04046895

Reaction notes

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