Sodium Hydroxide → 3H-Oxireno[i]isoquinoline-6,8(4H,7H)-dione, tetrahydro-7-methyl-4a-phenyl-

HRID 904758Notes

Reaction equation

HRID 904758 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[CH2:10][C:9]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:4](=[CH:5][CH2:6][CH2:7][CH2:8]2)[C:3]1=[O:19].ClC1C=CC=C(C(OO)=[O:28])C=1.[OH-].[Na+]>C(Cl)(Cl)Cl>[CH3:1][N:2]1[C:11](=[O:12])[CH2:10][C:9]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:4]3([O:28][CH:5]3[CH2:6][CH2:7][CH2:8]2)[C:3]1=[O:19]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 132819702-Methyl-4a-phenyl-4a,5,6,7-tetrahydroisoquinoline-1,3(2H,4H)-dione

Product 1

HCID 132820213H-Oxireno[i]isoquinoline-6,8(4H,7H)-dione, tetrahydro-7-methyl-4a-phenyl-Yield 65.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 1.0 g (3.92 mmoles) of N-methyl-4a-phenyl-1,3-diketo-1,2,3,4,4a,5,6,7-octahydroisoquinoline in 10 ml of chloroform was treated with a solution of 746 mg of 85% m-chloroperbenzoic acid in 12 ml of chloroform. The reaction mixture was refluxed for 36 hours, after which it was poured into 5 N sodium hydroxide. The aqueous phase was extracted twice with chloroform and the combined organic layers were washed well with water, then brine. Drying with sodium sulfate and evaporation of the solvent gave 0.7 g of white solid N-methyl-4a-phenyl-1,3-diketo-8,8a-epoxy-decahydroisoquinoline, mp 135°-140° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 36 hours
  2. extractionThe aqueous phase was extracted twice with chloroform
  3. washthe combined organic layers were washed well with water
  4. dry with materialDrying with sodium sulfate and evaporation of the solvent

Sources & evidence

ORD record
ord-a24da0d6ee7a4258b7d4bf46d9897424
Source dataset
uspto-grants-1983_12
Patent number
US04419517

Reaction notes

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