Acetic Acid → Hydrocotarnine

HRID 622196Notes

Reaction equation

HRID 622196 reaction equation
C(O[CH:4](OCC)[CH2:5][NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]2[O:14][CH2:15][O:16][C:10]=2[C:9]=1[O:17][CH3:18])C.S(=O)(=O)(O)O.[C:27](O)(=O)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]([CH3:27])[CH2:5][CH2:4]2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 13911324HCID 13911324, compound

Product 1

HCID 3646HydrocotarnineYield 93%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

1.19 g (5 mmol) of 4-hydroxy-8-methoxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline (1) obtained in Reference Example 1 or 2 was dissolved in 15 ml of acetic acid, to which 0.33 ml (6 mmol) of 97% sulfuric acid and 500 mg of 5% palladium on carbon catalyst were added to carry out catalytic reduction at 75° C. for 2 hours. The catalyst was filtered out and 2 ml of 25% aqueous sodium hydroxide solution and 5 ml of water were added to the reaction mixture, which was concentrated under vacuum. 10 ml of water was added to the residue, the solution was made basic with 25% aqueous sodium hydroxide solution and extracted with 10 ml and then 5 ml of methylene chloride successively. The liquid extract was washed with 5 ml of water, dried over anhydrous magnesium sulfate and then concentrated under vacuum to obtain 1.03 g of 8-methoxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline. Yield 93%.

Workup

  1. additionwere added
  2. customat 75° C.
  3. customfor 2 hours
  4. filtrationThe catalyst was filtered out and 2 ml of 25% aqueous sodium hydroxide solution and 5 ml of water
  5. additionwere added to the reaction mixture, which
  6. concentrationwas concentrated under vacuum
  7. addition10 ml of water was added to the residue
  8. extractionextracted with 10 ml
  9. extractionThe liquid extract
  10. washwas washed with 5 ml of water
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b3c6f25108b34d5099ab90d6e622185d
Source dataset
uspto-grants-1988_09
Patent number
US04769480

Reaction notes

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