Hydrochloric Acid → 8-Methoxy-6,7-methylenedioxyisoquinoline hydrochloride

HRID 1088924Notes

Reaction equation

HRID 1088924 reaction equation
C(O[CH:4](OCC)[CH2:5][N:6]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]2[O:24][CH2:25][O:26][C:20]=2[C:19]=1[O:27][CH3:28])S(C1C=CC(C)=CC=1)(=O)=O)C.[ClH:32].O>O1CCOCC1>[ClH:32].[CH3:28][O:27][C:19]1[C:20]2[O:26][CH2:25][O:24][C:21]=2[CH:22]=[C:23]2[C:18]=1[CH:17]=[N:6][CH:5]=[CH:4]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 13911325N-(2-methoxy-3,4-methylenedioxybenzyl)-N-(p-toluenesulfonyl)aminoacetaldehyde diethylacetal

Product 1

HCID 703645878-Methoxy-6,7-methylenedioxyisoquinoline hydrochlorideYield 61.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
5 °C

Procedure

N-(2-methoxy-3,4-methylenedioxybenzyl)-N-(p-toluenesulfonyl)aminoacetaldehyde diethylacetal (3) in an amount of 69.89 g (0.155 mol) was dissolved in 0.194 ml of dioxane, to which 14.7 ml (0.169 mol) of concentrated hydrochloric acid and 47.1 ml of water were added and heated under reflux for two hours and 40 minutes. After the mixture were cooled to about 5° C., deposited crystals were collected by filtration, washed with 30 ml of cold dioxcane and then dried to obtain 22.95 g of 8-methoxy-6,7-methylenedioxyisoquinoline hydrochloride (4) as yellow crystals. Yield 61.8%.

Workup

  1. additionwere added
  2. temperatureheated
  3. temperatureunder reflux for two hours and 40 minutes
  4. filtrationwere collected by filtration
  5. washwashed with 30 ml of cold dioxcane
  6. customdried

Sources & evidence

ORD record
ord-f5b6efdbe9ba42c389f6f8b54677e829
Source dataset
uspto-grants-1990_10
Patent number
US04963684

Reaction notes

Loading…