Sodium Hydroxide → 2-Phenyl-1,3,4,5-tetrahydrobenz[cd]indol-5-one

HRID 1637257Notes

Reaction equation

HRID 1637257 reaction equation
[C:1]1([CH:7]2[CH:15]3[CH2:16][CH2:17][C:18](=[O:19])[C:13]4[C:14]3=[C:9]([CH:10]=[CH:11][CH:12]=4)[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(Cl)C(Cl)=C(Cl)C(=O)C(=O)C=1Cl.[OH-].[Na+]>O1CCCC1>[C:1]1([C:7]2[NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[C:13]4[C:18](=[O:19])[CH2:17][CH2:16][C:15]=2[C:14]=34)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 73252o-ChloranilHCID 193482872-Phenyl-1,2,2a,3,4,5-hexahydrobenz[cd]indol-5-one

Product 1

HCID 193483682-Phenyl-1,3,4,5-tetrahydrobenz[cd]indol-5-oneYield 70.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A portion (3.3 g) of the compound obtained in Example 22 was dissolved in anhydrous tetrahydrofuran (THF; 400 ml) and to the solution was added o-chloranil (3.6 g). The resulting mixture was stirred for 30 minutes at room temperature. After adding 1N aqueous solution of sodium hydroxide, the reaction mixture was extracted twice with ethyl acetate. The organic layers were combined, washed twice with 1N aqueous solution of sodium hydroxide and once with saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (methylene chloride) and further crystallized from an ether/hexane mixed solvent to yield 2.3 g (70%) of the titled compound as crystals.

Workup

  1. extractionthe reaction mixture was extracted twice with ethyl acetate
  2. washwashed twice with 1N aqueous solution of sodium hydroxide and once with saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThen, the solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (methylene chloride)
  6. customfurther crystallized from an ether/hexane mixed solvent

Sources & evidence

ORD record
ord-132352bb25074d3bb14ad1e95960d078
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

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