Water → 4-Methoxy-[1,3]dioxolo[4,5-g]isoquinoline

HRID 1088925Notes

Reaction equation

HRID 1088925 reaction equation
Cl.[CH3:2][O:3][C:4]1[C:5]2[O:16][CH2:15][O:14][C:6]=2[CH:7]=[C:8]2[C:13]=1[CH:12]=[N:11][CH:10]=[CH:9]2.O.[OH-].[Na+]>C(Cl)Cl>[CH3:2][O:3][C:4]1[C:5]2[O:16][CH2:15][O:14][C:6]=2[CH:7]=[C:8]2[C:13]=1[CH:12]=[N:11][CH:10]=[CH:9]2

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 703645878-Methoxy-6,7-methylenedioxyisoquinoline hydrochloride

Product 1

HCID 213364-Methoxy-[1,3]dioxolo[4,5-g]isoquinolineYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

17.8 g (74.3 mmol) of the compound (4) thus obtained was added to 50 ml of water, which was then incorporated with 100 ml of methylene chloride and rendered basic with 25% aqueous solution of sodium hydroxide under water-cooling. After the solution was separated into two layers, the aqueous layer was extracted with 20 ml of methylene chloride. Then, the methylene chloride layers were combined and washed with 30 ml of water. They were dried over anhydrous magnesium sulfate and then concentrated at reduced pressure to obtain 15.06 g of 8-methoxy-6,7-methylenedioxyisoquinoline (5) with a yield of 99.7%. The resultant product was recrystallized from ethyl acetate/n-hexane: m.p. 144°-5° C. IR and NMR of the resultant product are listed below.

Workup

  1. temperaturecooling
  2. customAfter the solution was separated into two layers
  3. extractionthe aqueous layer was extracted with 20 ml of methylene chloride
  4. washwashed with 30 ml of water
  5. dry with materialThey were dried over anhydrous magnesium sulfate
  6. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-e10f26d42a48479aaf324e7d911d98bd
Source dataset
uspto-grants-1990_10
Patent number
US04963684

Reaction notes

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