Acetone → HCID 9922813, compound

HRID 2300582Notes

Reaction equation

HRID 2300582 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.[CH3:27][C:28]([CH3:30])=[O:29]>>[CH3:19][O:1][C:2]1([CH2:27][C:28](=[O:29])[CH3:30])[C:10](=[O:11])[C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[C:7]2[NH:6][C:5](=[O:16])[C:4]([CH3:18])([CH3:17])[C:3]1=2

Participants

5

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 178429195HCID 178429195, compound2×

Product 1

HCID 9922813HCID 9922813, compound

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 acetone (5 mL) was added K2CO3 (0.132 g, 0.96 mmol) while stirring at RT. After 10 minutes, MeI (0.058 g, 0,41 mmol) was added via a syringe and the mixture was allowed to stir for 1 h followed by addition of more MeI (0.058 g, 0,41 mmol) and the reaction was stirred over night. The solvent was removed in vacuum and the solid was dissolved in CHCl3, filtered and purified by preparative HPLC. Yield: 64 mg (50%). 1H NMR (400 MHz, CDCl3) δ 1.46 (d, 6 H), 2.12 (s, 3 H), 2.90 (s, 2 H), 3.65 (s, 3 H), 7.42 (t, 1 H), 7.55 (t, 1 H), 7.78 (d, 1 H), 7.94 (d, 1 H): MS (CI) m/z 314.36 (M+1).

Workup

  1. stirringto stir for 1 h
  2. stirringthe reaction was stirred over night
  3. customThe solvent was removed in vacuum
  4. dissolutionthe solid was dissolved in CHCl3
  5. filtrationfiltered
  6. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-3f25727a9d604b2c9ae194be7eb9ff65
Source dataset
uspto-grants-2002_12
Patent number
US06498182B2

Reaction notes

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