Methyl iodide → 2-Methyl-6,7,8-trimethoxy-3,4-dihydro-isoquinolinium iodide

HRID 1155503Notes

Reaction equation

HRID 1155503 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([O:15][CH3:16])[C:12]=1[O:13][CH3:14])[CH:9]=[N:8][CH2:7][CH2:6]2.[CH3:17][I:18]>CC(C)=O>[I-:18].[CH3:17][N+:8]1[CH2:7][CH2:6][C:5]2[C:10](=[C:11]([O:15][CH3:16])[C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:9]=1

Participants

4

Reactant 2

HCID 6328Methyl iodide2×HCID 47377136,7,8-Trimethoxy-3,4-dihydroisoquinoline

Product 1

HCID 128990142-Methyl-6,7,8-trimethoxy-3,4-dihydro-isoquinolinium iodide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.9 kg of 6,7,8-trimethoxy-3,4-dihydro-isoquinoline and 7 liters of acetone are added to a reactor, followed by 2.1 kg of methyl iodide, the temperature being kept below 50°. The reaction mixture is then heated under reflux for 30 minutes, a further 200 g of methyl iodide is added, and the mixture is refluxed for about a further hour.

Workup

  1. custombeing kept below 50°
  2. temperatureThe reaction mixture is then heated
  3. temperatureunder reflux for 30 minutes
  4. temperaturethe mixture is refluxed for about a further hour

Sources & evidence

ORD record
ord-2c30490217d749f4bfd474f671398971
Source dataset
uspto-grants-1981_11
Patent number
US04302458

Reaction notes

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