Sodium Methoxide → 6-Methoxy-2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

HRID 276916Notes

Reaction equation

HRID 276916 reaction equation
[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:11]2[NH:10][C:9](=[O:14])[C:8]3([CH2:18][CH2:19][CH2:20][CH2:21][Br:22])[CH2:15][CH2:16][CH2:17][C:6]=1[C:7]=23)(=O)C.C[O-].[Na+]>CO>[CH3:1][O:4][C:5]1[CH:13]=[CH:12][C:11]2[NH:10][C:9](=[O:14])[C:8]3([CH2:18][CH2:19][CH2:20][CH2:21][Br:22])[CH2:15][CH2:16][CH2:17][C:6]=1[C:7]=23

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 226295546-Acetoxy-2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

Product 1

HCID 117274696-Methoxy-2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-oneYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 16 ml portion of methanol solution of 6-acetoxy-2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one (0.60 g, 1.64 mmol) was mixed with sodium methoxide and stirred at a room temperature for 3 hours. After neutralization of the reaction solution with an ion exchange resin Amberlite 15, the resin was removed by filtration and the solvent was evaporated under a reduced pressure. The thus obtained oily substance was dissolved in 4 ml of acetone, and the solution was mixed with 2 ml of methyl iodide and 2 ml of potassium carbonate aqueous solution and stirred overnight at room temperature. The reaction solution was extracted with ethyl acetate and washed with 1 N hydrochloric acid. After drying (Na2SO4), the solvent was evaporated under a reduced pressure, and the thus obtained oily substance was purified by a silica gel column chromatography (100 cc; elution with ethyl acetate-hexane=1:2) to obtain 0.31 g of the title compound (56% in yield).

Workup

  1. customAfter neutralization of the reaction solution with an ion exchange resin Amberlite 15, the resin was removed by filtration
  2. customthe solvent was evaporated under a reduced pressure
  3. dissolutionThe thus obtained oily substance was dissolved in 4 ml of acetone
  4. additionthe solution was mixed with 2 ml of methyl iodide and 2 ml of potassium carbonate aqueous solution
  5. stirringstirred overnight at room temperature
  6. extractionThe reaction solution was extracted with ethyl acetate
  7. washwashed with 1 N hydrochloric acid
  8. dry with materialAfter drying (Na2SO4)
  9. customthe solvent was evaporated under a reduced pressure
  10. customthe thus obtained oily substance was purified by a silica gel column chromatography (100 cc; elution with ethyl acetate-hexane=1:2)

Sources & evidence

ORD record
ord-f50b98002a5b4e619be83b1dd7fb6cb9
Source dataset
uspto-grants-2002_03
Patent number
US06355642B1

Reaction notes

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