m-Chloroperbenzoic acid → HCID 19833162, compound

HRID 2051358Notes

Reaction equation

HRID 2051358 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2C3[CH2:7][CH2:8][CH2:9][N:10]([C:14]([NH2:16])=[O:15])[C:11]=3[CH2:12][CH2:13][C:4]=2[CH:3]=1.ClC1C=CC=C(C(OO)=[O:27])C=1.[C:30](=[O:33])([O-])O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[C:30](=[O:33])[CH2:7][CH2:8][CH2:9][N:10]([C:14]([NH2:16])=[O:15])[C:11](=[O:27])[CH2:12][CH2:13][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 19833172HCID 19833172, compound

Product 1

HCID 19833162HCID 19833162, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

9.20 g (0.035 mol) of 8-chloro-2,3,5,6-tetrahydrobenzo[f]quinoline-4(1H)-carboxamide are suspended in 100 ml of methylene chloride and 14.1 g (0.071 mol) of m-chloroperbenzoic acid (85 percent) in 150 ml of methylene chloride are added dropwise thereto at 10-15°. After stirring at room temperature for 1.5 hours, the mixture is poured into saturated sodium hydrogen carbonate solution, extracted with methylene chloride, dried with magnesium sulfate and the solvent is distilled in a vacuum. The solid obtained is washed with hot ethyl acetate. Recrystallization from dioxane/ether yields 11-chloro-2,3,5,6,7,8-hexahydro-3,8-dioxo-4-benzazecine -4(1H)-carboxamide as white crystals with melting point 182-184°.

Workup

  1. customat 10-15°
  2. extractionextracted with methylene chloride
  3. dry with materialdried with magnesium sulfate
  4. distillationthe solvent is distilled in a vacuum
  5. customThe solid obtained
  6. washis washed with hot ethyl acetate
  7. customRecrystallization from dioxane/ether

Sources & evidence

ORD record
ord-ec2feb7aa7ce480982ba316d94954d58
Source dataset
uspto-grants-1991_05
Patent number
US05017608

Reaction notes

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