Methyl iodide → HCID 9921332, compound

HRID 2300581Notes

Reaction equation

HRID 2300581 reaction equation
[OH:1][C:2]1[C:10](=[O:11])[C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[C:7]2[C:3]=1[C:4]([CH3:18])([CH3:17])[C:5](=[O:16])[N:6]=2.[C:19]([O-])([O-])=O.[K+].[K+].CI>CO>[CH3:19][O:1][C:2]1[C:10](=[O:11])[C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[C:7]2[C:3]=1[C:4]([CH3:18])([CH3:17])[C:5](=[O:16])[N:6]=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178429195HCID 178429195, compound2×

Product 1

HCID 9921332HCID 9921332, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-hydroxy-3,3-dimethyl-2H-benzo[g]indole-2,5(3H)-dione (compound 1) (0.1 g, 0.415 mmol) in MeOH (5 mL) was added K2CO3 (0.132 g, 0.96 mmol) while stirring at RT. After 10 min. MeI (100 μL, 0.228 g, 1.6 mmol) was added via a syringe and the mixture was allowed to stirred over night. The solvent was removed in vacuum and the solid was dissolved in CHCl3, filtered and purified by prep. HPLC (SF/CHCl3). Yield: 0.051 mg (50%). 1H NMR (400 MHz, CDCl3) δ 1.48 (s, 6 H), 3.68 (s, 3 H), 7.58 (t, 1 H), 7.68 (t, 1 H), 8.02 (d, 1 H), 8.23 (d, 1 H). MS (CI) m/z: 256.31 (M+1).

Workup

  1. stirringto stirred over night
  2. customThe solvent was removed in vacuum
  3. dissolutionthe solid was dissolved in CHCl3
  4. filtrationfiltered
  5. custompurified by prep

Sources & evidence

ORD record
ord-9c1ee2895f414c1584c013c40a440913
Source dataset
uspto-grants-2002_12
Patent number
US06498182B2

Reaction notes

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