Sulfuric Acid → Hydrocotarnine

HRID 845836Notes

Reaction equation

HRID 845836 reaction equation
C(O[CH:4]1[C:13]2[C:8](=[C:9]([O:17][CH3:18])[C:10]3[O:16][CH2:15][O:14][C:11]=3[CH:12]=2)[CH2:7][N:6]([CH3:19])[CH2:5]1)C.S(=O)(=O)(O)O>C(O)(=O)C.[C].[Pd]>[CH3:18][O:17][C:9]1[C:10]2[O:16][CH2:15][O:14][C:11]=2[CH:12]=[C:13]2[C:8]=1[CH2:7][N:6]([CH3:19])[CH2:5][CH2:4]2

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 13912215HCID 13912215, compound

Product 1

HCID 3646HydrocotarnineYield 89%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

0.27 g (1.02 mmol) of 4-ethoxy-8-methoxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline (8) was dissolved in 15 ml of acetic acid, and the solution was added with 200 mg of 5% palladium carbon and 0.1 ml of 97% sulfuric acid and hydrogenated at 75° C. for 1 hour and 40 minutes. After cooling, the catalyst was filtered off and the filtrate was added with a small quantity of an aqueous solution of sodium hydroxide and concentrated under reduced pressure. The residue was added with 10 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 0.20 g of 8-methoxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline (13) as a crystal. Yield: 89%.

Workup

  1. temperatureAfter cooling
  2. filtrationthe catalyst was filtered off
  3. additionthe filtrate was added with a small quantity of an aqueous solution of sodium hydroxide
  4. concentrationconcentrated under reduced pressure
  5. additionThe residue was added with 10 ml of water
  6. extractionThe resulted solution was extracted twice with 5 ml of methylene chloride
  7. washthe extract was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4f02ca4e042d4c9093b7f4640aad56e2
Source dataset
uspto-grants-1988_07
Patent number
US04760145

Reaction notes

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