HCID 13912216, compound → Hydrocotarnine

HRID 845835Notes

Reaction equation

HRID 845835 reaction equation
C(O[CH:5]1[C:14]2[C:9](=[C:10]([O:18][CH3:19])[C:11]3[O:17][CH2:16][O:15][C:12]=3[CH:13]=2)[CH2:8][N:7]([CH3:20])[CH2:6]1)(=O)C>[C].[Pd].C(O)C>[CH3:19][O:18][C:10]1[C:11]2[O:17][CH2:16][O:15][C:12]=2[CH:13]=[C:14]2[C:9]=1[CH2:8][N:7]([CH3:20])[CH2:6][CH2:5]2

Participants

4

Reactant 1

HCID 13912216HCID 13912216, compound

Product 1

HCID 3646HydrocotarnineYield 86%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

0.28 g (1 mmol) of 4-acetoxy-8-methoxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline (9) was added to 4 ml of ethanol. This solution was then added with 100 mg of 5% palladium carbon and hydrogenated at room temperature. After the reaction was completed, the catalyst was filtered off and the solvent was distilled off under reduced pressure. The residue was added with 5 ml of water and made basic with an aqueous solution of sodium hydroxide. The resulted solution was extracted twice with 5 ml of methylene chloride and the extract was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 0.19 g of 8-methoxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline (13) as a crystal. Yield: 86%.

Workup

  1. filtrationthe catalyst was filtered off
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionThe residue was added with 5 ml of water
  4. extractionThe resulted solution was extracted twice with 5 ml of methylene chloride
  5. washthe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b2c7a2a7d8d5457597d04a76e950ef89
Source dataset
uspto-grants-1988_07
Patent number
US04760145

Reaction notes

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