Methyl iodide → 1,2,9,10-Tetramethoxy-6-methyl-7-oxo-7H-dibenzo[de,g]quinolin-6-ium iodide

HRID 838930Notes

Reaction equation

HRID 838930 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[C:11]2[C:15]3[C:20]([C:21](=[O:22])[C:9]4=[C:10]2[C:5](=[CH:6][CH:7]=[N:8]4)[CH:4]=1)=[CH:19][C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3.[I:27][CH3:28]>CC(C)=O>[CH3:28][N+:8]1[CH:7]=[CH:6][C:5]2[C:10]3=[C:11]([C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[C:15]2[C:20]([C:21](=[O:22])[C:9]=13)=[CH:19][C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2.[I-:27]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 97662Oxoglaucine2×

Product 1

HCID 416801,2,9,10-Tetramethoxy-6-methyl-7-oxo-7H-dibenzo[de,g]quinolin-6-ium iodide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Oxoglaucine methiodide was prepared from oxoglaucine in accordance with the process of Example V. A 31 mg sample of oxoglaucine was refluxed in 8 ml of acetone until it completely dissolved (approximately 30 minutes) and then 0.75 ml of iodomethane was added. The solution was refluxed until it became brown. The crystals were then collected by filtration to yield 15 mg of the methiodide salt, mp 255 d.

Workup

  1. dissolutioncompletely dissolved (approximately 30 minutes)
  2. temperatureThe solution was refluxed until it
  3. filtrationThe crystals were then collected by filtration

Sources & evidence

ORD record
ord-b882f16c4ef2405baf31e5f047788dca
Source dataset
uspto-grants-1978_06
Patent number
US04093717

Reaction notes

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