m-Chloroperbenzoic acid → HCID 86743679, compound

HRID 329751Notes

Reaction equation

HRID 329751 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:16]([NH:18][CH:19]2[CH:24]3[CH2:25][CH2:26][N:21]([CH2:22][CH2:23]3)[CH2:20]2)=[O:17])[C:5]2[O:10][CH:9]([CH2:11][CH3:12])[C:8](=[O:13])[N:7]([CH3:14])[C:6]=2[CH:15]=1.ClC1C=CC=C(C(OO)=[O:35])C=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:16]([NH+:18]([O-:35])[CH:19]2[CH:24]3[CH2:25][CH2:26][N:21]([CH2:22][CH2:23]3)[CH2:20]2)=[O:17])[C:5]2[O:10][CH:9]([CH2:11][CH3:12])[C:8](=[O:13])[N:7]([CH3:14])[C:6]=2[CH:15]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14719850HCID 14719850, compound

Product 1

HCID 86743679HCID 86743679, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2.6 g of 6-chloro-2-ethyl-3,4-dihydro-4-methyl-3-oxo-N-(3-quinuclidinyl)-2H-1,4-benzoxazine-8-carboxamide in 100 ml of chloroform is added portionwise 1.9 g of metachloroperbenzoic acid under cooling and stirring. After 0.5 hour, ammonia gas is bubbled through the reaction solution under stirring and the precipitate is filtered off. The mother liquor is distilled off under reduced pressure followed by recrystallizing the residue from ethanol-isopropyl ether to give 6-chloro-2-ethyl-3,4-dihydro-4-methyl-3-oxo-N-(3-quinuclidinyl)-2H-1,4- benzoxazine-8-carboxamide N-oxide.

Workup

  1. temperatureunder cooling
  2. customammonia gas is bubbled through the reaction solution
  3. stirringunder stirring
  4. filtrationthe precipitate is filtered off
  5. distillationThe mother liquor is distilled off under reduced pressure
  6. customby recrystallizing the residue from ethanol-isopropyl ether

Sources & evidence

ORD record
ord-d7e167a78f564020b8076e69cac9e9fc
Source dataset
uspto-grants-1990_01
Patent number
US04892872

Reaction notes

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