Diethyl Sulfate → 1-Ethylbenz(cd)indol-2(1H)-one

HRID 2291260Notes

Reaction equation

HRID 2291260 reaction equation
[NH:1]1[C:9]2[C:4]3[C:5](=[CH:10][CH:11]=[CH:12][C:3]=3[C:2]1=[O:13])[CH:6]=[CH:7][CH:8]=2.S(OCC)(O[CH2:18][CH3:19])(=O)=O>[OH-].[K+]>[CH2:18]([N:1]1[C:9]2[C:4]3[C:5](=[CH:10][CH:11]=[CH:12][C:3]=3[C:2]1=[O:13])[CH:6]=[CH:7][CH:8]=2)[CH3:19]

Participants

4

Reactant 2

HCID 6163Diethyl SulfateHCID 67222benz(cd)indol-2(1H)-one

Product 1

HCID 745921-Ethylbenz(cd)indol-2(1H)-oneYield 46%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

A mixture of benz[cd]indol-2(1H)-one (15.0 g, 88.8 mmole) in 20% aqueous potassium hydroxide (200 ml) was heated at 55°-60° C. while 60 ml of diethyl sulfate was added dropwise over a three hour period. After 16 hours at room temperaure and an additional hour at 55°-60° C., the mixture was partitioned between dichloromethane and water. The organic phase was concentrated and purified by chromatography on silicon dioxide with 5% acetone/dichloromethane to give the desired product (8.0 g, 46%).

Workup

  1. additionwas added dropwise over a three hour period
  2. customan additional hour at 55°-60° C., the mixture was partitioned between dichloromethane and water
  3. concentrationThe organic phase was concentrated
  4. custompurified by chromatography on silicon dioxide with 5% acetone/dichloromethane

Sources & evidence

ORD record
ord-e9bf83fa9f92471f9c5abf636c2b06e0
Source dataset
uspto-grants-1989_01
Patent number
US04795712

Reaction notes

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