Benzene → Indol-6-one

HRID 1156292Notes

Reaction equation

HRID 1156292 reaction equation
C1C=CC=CC=1.CI.[OH-:9].[Na+].C([N+:15]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:20][CH2:21][CH2:22][CH3:23])CCCC)CCC>O>[N:15]1[C:20]2[C:26]([CH:27]=[CH:23][C:22](=[O:9])[CH:21]=2)=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 16028Tetrabutylammonium

Product 1

HCID 17925780Indol-6-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5 g of 3,4-dihydro-1H-cyclohept[c,d] indol-6-one, 50 ml of benzene, 2.5 ml of methyl iodide, 25 ml of 5 N sodium hydroxide solution and 9.2 g of tetra-n-butyl ammonium acid sulfate was stirred for 30 minutes under an inert atmosphere at 40°-45° C. and the mixture was diluted with water. The decanted aqueous phase was extracted with ethyl acetate and the organic phase was washed with N hydrochloride acid, with water, dried and evaporated to dryness. The residue was chromatographed over silica gel and was eluted with a 95-5 chloroform-ethyl acetate mixture to obtain 6.5 g of raw product. The latter was crystallized from isopropanol to obtain 5.15 g of 1-methyl-1,3,4,5-tetrahydro-6H-cyclohept [c,d,] indol-6-one melting at ≃70° C.

Workup

  1. extractionThe decanted aqueous phase was extracted with ethyl acetate
  2. washthe organic phase was washed with N hydrochloride acid, with water
  3. customdried
  4. customevaporated to dryness
  5. customThe residue was chromatographed over silica gel
  6. washwas eluted with a 95-5 chloroform-ethyl acetate mixture
  7. customto obtain 6.5 g of raw product
  8. customThe latter was crystallized from isopropanol

Sources & evidence

ORD record
ord-1ddd7d26fa8f4e4ba184094402c8af7e
Source dataset
uspto-grants-1982_06
Patent number
US04335135

Reaction notes

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