Hydrochloric Acid → 7-Methoxy-1-methylisoquinoline

HRID 127923Notes

Reaction equation

HRID 127923 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][CH:27]=1)[CH:6]([N:8]([CH2:19][CH:20](OC)OC)S(C1C=CC(C)=CC=1)(=O)=O)[CH3:7].O1CCOCC1.Cl>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:25]([CH:20]=[CH:19][N:8]=[C:6]2[CH3:7])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 20523222HCID 20523222, compound

Product 1

HCID 159337467-Methoxy-1-methylisoquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 39.3 g. (0.1 mole) of 3-methoxy-α-methyl-N-(2,2-dimethoxyethyl)-N-tosyl-benzylamine, one liter of dioxane and 80 ml. of 6 N hydrochloric acid is refluxed for six hours and allowed to stand for sixteen hours. The mixture is poured into two liters of water and extracted with ether. The aqueous phase is made alkaline with concentrated ammonium hydroxide and extracted with chloroform. The chloroform extract is washed, dried and evaporated to yield 7-methoxy-1-methylisoquinoline.

Workup

  1. additionA mixture of 39.3 g
  2. waitto stand for sixteen hours
  3. extractionextracted with ether
  4. extractionextracted with chloroform
  5. extractionThe chloroform extract
  6. washis washed
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-f7361eb8210f458ca9fdcddc43a7b065
Source dataset
uspto-grants-1981_03
Patent number
US04258049

Reaction notes

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