m-Chloroperbenzoic acid → HCID 86743677, compound

HRID 329750Notes

Reaction equation

HRID 329750 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([NH:15][CH:16]2[CH:21]3[CH2:22][CH2:23][N:18]([CH2:19][CH2:20]3)[CH2:17]2)=[O:14])[C:5]2[O:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=2[CH:12]=1.ClC1C=CC=C(C(OO)=[O:32])C=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([NH+:15]([O-:32])[CH:16]2[CH:21]3[CH2:22][CH2:23][N:18]([CH2:19][CH2:20]3)[CH2:17]2)=[O:14])[C:5]2[O:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=2[CH:12]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14719837HCID 14719837, compound

Product 1

HCID 86743677HCID 86743677, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4.8 g of 6-chloro-3,4-dihydro-3-oxo-N-(3-quinuclidinyl)-2H-1,4-benzoxazine-8-carboxamide in 150 ml of chloroform is added portionwise 3.7 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-3,4-dihydro-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-a8853e67258c4fab9cd6d80035c607be
Source dataset
uspto-grants-1990_01
Patent number
US04892872

Reaction notes

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