Water → HCID 457730, compound

HRID 1683149Notes

Reaction equation

HRID 1683149 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14](=[O:15])[C:3]=12.[OH2:16]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][N+:5]([O-:16])=[C:4]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14](=[O:15])[C:3]=12

Participants

4

Reactant 2

HCID 962WaterHCID 72584Onychine

Product 1

HCID 457730HCID 457730, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 12.7 g (0.065 mol) of 4-methyl-5H-indeno[3,2-b]-pyridin-5-one in 550 ml of chloroform was added dropwise at 25° C. to a solution of 13 g (0.066 mol) of water-moist 3-chloroperbenzoic acid in 500 ml of chloroform. After stirring at room temperature for 12 hours, the mixture was washed twice with 50 ml each of a saturated aqueous sodium hydrogen carbonate solution and then with water, dried over Na2SO4 and concentrated under reduced pressure. The residue was crystallized at 0° C. using 20 ml of diethyl ether. 12.4 g (90.5% of theory) of 4-methyl-5H-indeno[3,2-b]pyridin-5-one-N-oxide were obtained as white crystals of m.p. 218°-220° C.

Workup

  1. washthe mixture was washed twice with 50 ml each of a saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialwith water, dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was crystallized at 0° C.

Sources & evidence

ORD record
ord-18e1a876342e4166adbb50e76fdc670c
Source dataset
uspto-grants-1997_06
Patent number
US05637554

Reaction notes

Loading…