Dimethyl Sulfate → HCID 14820228, compound

HRID 1088926Notes

Reaction equation

HRID 1088926 reaction equation
[CH3:1][O:2][C:3]1[C:4]2[O:15][CH2:14][O:13][C:5]=2[CH:6]=[C:7]2[C:12]=1[CH:11]=[N:10][CH:9]=[CH:8]2.[S:16]([O:21]C)([O:19][CH3:20])(=[O:18])=[O:17]>C1(C)C=CC=CC=1>[CH3:20][O:19][S:16]([O-:21])(=[O:18])=[O:17].[CH3:1][O:2][C:3]1[C:4]2[O:15][CH2:14][O:13][C:5]=2[CH:6]=[C:7]2[C:12]=1[CH:11]=[N+:10]([CH3:20])[CH:9]=[CH:8]2

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 213364-Methoxy-[1,3]dioxolo[4,5-g]isoquinoline

Product 1

HCID 14820228HCID 14820228, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

8-Methoxy-6,7-methylenedioxyisoquinoline (5) in an amount of 2.03 g (10 mmol) was dissolved into 40 ml of toluene while heating them at 60° C. Then, 1.13 ml (12 mmol) of dimethyl sulfate was added and stirred at 60° C. for 4 hours. After cooling, deposited crystals were collected by filtration, washed with toluene and then dried to obtain 3.30 g of 8-methoxy-2-methyl-6,7-methylenedioxyisoquinolinium methyl sulfate (6) with a yield of 100%. The resultant product was then recrystallized from ethanol: m.p. 172°-4° C. IR and NMR of the resultant product are listed below.

Workup

  1. temperatureAfter cooling
  2. filtrationdeposited crystals were collected by filtration
  3. washwashed with toluene
  4. customdried

Sources & evidence

ORD record
ord-784a469d1379470badc29c16ff04ad27
Source dataset
uspto-grants-1990_10
Patent number
US04963684

Reaction notes

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