Potassium Iodide → HCID 19833137, compound

HRID 2051334Notes

Reaction equation

HRID 2051334 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([O:10]O)=O)[CH:3]=1.[C:12]([N:15]1C2CCC3C=CC=C(Cl)[C:20]=3[C:19]=2[CH2:18][CH2:17][CH2:16]1)(=[O:14])[CH3:13].[I-].[K+].S([O-])([O-])(=[O:34])=S.[Na+].[Na+].[CH:39]([Cl:42])(Cl)Cl>O>[C:12]([N:15]1[CH2:16][CH2:17][CH2:18][C:19](=[O:34])[C:20]2[C:39]([Cl:42])=[CH:3][CH:2]=[CH:7][C:6]=2[CH2:5][CH2:4][C:8]1=[O:10])(=[O:14])[CH3:13]

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 6212Chloroform2×HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 19833130HCID 19833130, compound

Product 1

HCID 19833137HCID 19833137, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

16 0 g of 85 percent m-chloroperbenzoic acid in 205 ml of chloroform are added at 0 to 5° to a solution of 8.50 g of 4-acetyl-10-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline in 205 ml of chloroform. After stirring at room temperature for 4 hours, the mixture is treated with 4 g of potassium iodide and 70 ml of water and with sodium thiosulfate until decolorization occurs. The chloroform phase is washed with 70 ml of 2N sodium hydroxide solution and twice with 170 ml of water and evaporated in a vacuum. Chromatography on 100 g of silica gel with methylene chloride yields 4-acetyl-9-chloro-1,2,4,5,6,7-hexahydro -4-benzazecine-3,8-dione with a melting point of 115-116° after recrystallization from isopropyl ether.

Workup

  1. washThe chloroform phase is washed with 70 ml of 2N sodium hydroxide solution and twice with 170 ml of water
  2. customevaporated in a vacuum

Sources & evidence

ORD record
ord-41e8a4de748d4ba7bfda5f01ad8eeb5c
Source dataset
uspto-grants-1991_05
Patent number
US05017608

Reaction notes

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