Water → 11-Chloro-1,2,4,5,6,7-hexahydro-4-benzazecine-3,8-dione

HRID 569654Notes

Reaction equation

HRID 569654 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[C:6]3[CH2:7][CH2:8][CH2:9][NH:10][C:11]=3[CH2:12][CH2:13][C:4]=2[CH:3]=1.[Mn]([O-])(=O)(=O)=[O:17].[K+].I([O-])(=O)(=O)=O.[Na+].[OH2:28]>C(Cl)Cl.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[C:6](=[O:17])[CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:28])[CH2:12][CH2:13][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 516875Potassium PermanganateHCID 198331348-Chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinolineHCID 23667635Sodium periodate

Product 1

HCID 1983315911-Chloro-1,2,4,5,6,7-hexahydro-4-benzazecine-3,8-dione

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

26.3 g (0.12 mol) of 8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline dissolved in 3 l of methylene chloride were added to a solution of 4.75 g (0.03 mol) of potassium permanganate and 514 g (2.4 mol) of sodium periodate in 12 l of water, 3.00 g (0.013 mol) of benzyltriethylammonium chloride were added thereto and the mixture was stirred at room temperature overnight. The mixture was filtered over Dicalit and extracted with methylene chloride. Drying with sodium sulphate, distillation of the solvent in vacuo and chromatography (silica gel, ethyl acetate) gave 11-chloro-1,2,4,5,6,7-hexahydro-4-benzazecine-3,8-dione as beige crystals of melting point 142°-144°.

Workup

  1. additionwere added
  2. filtrationThe mixture was filtered over Dicalit
  3. extractionextracted with methylene chloride
  4. dry with materialDrying with sodium sulphate, distillation of the solvent in vacuo and chromatography (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-0882e5545017470dad32071419f7c0fc
Source dataset
uspto-grants-1988_03
Patent number
US04732979

Reaction notes

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