Water → HCID 13912216, compound

HRID 845832Notes

Reaction equation

HRID 845832 reaction equation
[OH:1][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.O.[OH-].[Na+].[C:21](Cl)(=[O:23])[CH3:22]>C(Cl)Cl>[C:21]([O:1][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)(=[O:23])[CH3:22]

Participants

6

Reactant 4

HCID 962Water2×HCID 6367Acetyl chlorideHCID 14798Sodium HydroxideHCID 13912214HCID 13912214, compound

Product 1

HCID 13912216HCID 13912216, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.74 g (20 mmol) of 4-hydroxy-8-methoxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline (6) was dissolved in 70 ml of methylene chloride, to which 1.71 ml of acetyl chloride was added dropwise at room temperature. This solution was stirred at 20°-30° C. for one hour, added with 30 ml of water and then further added with 25% aqueous solution of sodium hydroxide to make the water layer basic. After separating the layers, the water layer was extracted with 20 ml of methylene chloride. The methylene chloride layers were joined together and washed with 30 ml of water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain 5.53 g of 4-acetoxy-8-methoxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline (9) as a crystal (yield: 99%). This was then recrystallized from ethanol/n-hexane. Melting point: 109°-110° C.

Workup

  1. additionwas added dropwise at room temperature
  2. customAfter separating the layers
  3. extractionthe water layer was extracted with 20 ml of methylene chloride
  4. washwashed with 30 ml of water
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-fed95290e5f64c5fbd26ed4856796e97
Source dataset
uspto-grants-1988_07
Patent number
US04760145

Reaction notes

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