Sulfuric Acid → Hydrocotarnine

HRID 845834Notes

Reaction equation

HRID 845834 reaction equation
O[CH:2]1[C:11]2[C:6](=[C:7]([O:15][CH3:16])[C:8]3[O:14][CH2:13][O:12][C:9]=3[CH:10]=2)[CH2:5][N:4]([CH3:17])[CH2:3]1.S(=O)(=O)(O)O>C(O)(=O)C.[C].[Pd]>[CH3:16][O:15][C:7]1[C:8]2[O:14][CH2:13][O:12][C:9]=2[CH:10]=[C:11]2[C:6]=1[CH2:5][N:4]([CH3:17])[CH2:3][CH2:2]2

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 13912214HCID 13912214, compound

Product 1

HCID 3646HydrocotarnineYield 93.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

1.19 g (5 mmol) of 4-hydroxy-8-methoxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline (6) was dissolved in 15 ml of acetic acid, and this solution was subjected to catalytic reduction for 2 hours at 75° C. by adding 0.33 ml (6 mmol) of 97% sulfuric acid and 500 mg of 5% palladium carbon. The catalyst was filtered off, and the filtrate was added with 2 ml of 25% aqueous solution of sodium hydroxide and 5 ml of water and then concentrated under reduced pressure. The residue was added with 10 ml of water, made basic with 25% aqueous solution of sodium hydroxide under ice cooling and extracted with 10 ml and then with 5 ml of methylene chloride successively. The extract layer was washed with 5 ml of water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 1.03 g of 8-methoxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline. Yield: 93%.

Workup

  1. filtrationThe catalyst was filtered off
  2. additionthe filtrate was added with 2 ml of 25% aqueous solution of sodium hydroxide and 5 ml of water
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was added with 10 ml of water
  5. extractionextracted with 10 ml
  6. washThe extract layer was washed with 5 ml of water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7dee34cb11aa4c37ab23900d845b3034
Source dataset
uspto-grants-1988_07
Patent number
US04760145

Reaction notes

Loading…