Methyl iodide → HCID 20039734, compound

HRID 1762809Notes

Reaction equation

HRID 1762809 reaction equation
[CH:1]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:2]=1[CH2:3][C:4]1[N:5]([CH:11]=[C:12]3[C:17]=1[C:16](=[O:18])[C:15]1[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=1[C:13]3=[O:23])[CH2:6]2.[C:24](=O)([O-])[O-].[K+].[K+].IC>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(#N)C.ClCCl>[CH3:24][CH:3]1[C:2]2[C:7](=[CH:8][CH:9]=[CH:10][CH:1]=2)[CH2:6][N:5]2[CH:11]=[C:12]3[C:17]([C:16](=[O:18])[C:15]4[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=4[C:13]3=[O:23])=[C:4]12

Participants

7

Reactant 3

HCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 71772Mitoquidone2×

Product 1

HCID 20039734HCID 20039734, compoundYield 9.8%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5,14-dihydrobenz[5,6]isoindolo[2,1-b]isoquinoline-8,13-dione (0.96 g) (Intermediate 1), benzyl triethylammonium chloride (0.16 g), potassium carbonate (2.20 g) and iodomethane (0.45 ml) in acetonitrile (100 ml) was stirred and heated under reflux for 4 h. A further portion of iodomethane (0.5 ml) was added and the mixture was stirred at 80° C. for 1 h. The mixture was cooled to room temperature, diluted with dichloromethane (250 ml) and filtered. The filtrate was concentrated in vacuo and the residue was purified on preparative plates eluting five times with chloroform to give the title compound (98 mg) m.p. 215°-218° C. λmax (in CHCl3) 246.5 nm (ε51,050), 266.5 nm (ε18,250) and 366.55 nm (ε3,700).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 h
  3. stirringthe mixture was stirred at 80° C. for 1 h
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified on preparative plates
  7. washeluting five times with chloroform

Sources & evidence

ORD record
ord-840537cf7f7a408c894e6692af625f16
Source dataset
uspto-grants-1989_05
Patent number
US04835158

Reaction notes

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