Potassium Iodide → HCID 19833137, compound

HRID 1639369Notes

Reaction equation

HRID 1639369 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-6961a02f18d74d3eb226258935c091e2
Source dataset
uspto-grants-1989_11
Patent number
US04883815

Reaction notes

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