Water → HCID 71224964, compound

HRID 1855111Notes

Reaction equation

HRID 1855111 reaction equation
[C:1]([O:5][C:6]([C:8]1[C:13]([NH2:14])=[CH:12][CH:11]=[C:10]([CH3:15])[N:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:24])C=1.O.[OH-].[Na+]>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([C:8]1[C:13]([NH2:14])=[CH:12][CH:11]=[C:10]([CH3:15])[N+:9]=1[O-:24])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 71224956HCID 71224956, compound

Product 1

HCID 71224964HCID 71224964, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

20.37 g (92.2 mmol) of 2-t-butoxycarbonyl amino-6-methylpyridine was dissolved in 100 mL of chloroform, and the resulting solution was cooled with ice water. 25 g (101.4 mmol) of a 70% by weight product of meta-chloroperbenzoic acid was added thereto. After confirming that there is no large heat generation, the temperature was raised to room temperature. After 2 hours had elapsed, 20 mL of water was added thereto. Then, the pH was adjusted to 14 by adding an aqueous solution of caustic soda having a concentration of 28%. Following liquid separation, the resulting aqueous layer was extracted with chloroform. The chloroform layer was washed with a 28% aqueous solution of caustic soda and then with water, and then dried with magnesium sulfate. Chloroform was removed by distillation under reduced pressure to obtain 21.30 g of 2-t-butoxycarbonyl amino-6-methylpyridine-N-oxide (yield: 99.6%) in a light orange oily form.

Workup

  1. customliquid separation
  2. extractionthe resulting aqueous layer was extracted with chloroform
  3. washThe chloroform layer was washed with a 28% aqueous solution of caustic soda
  4. dry with materialwith water, and then dried with magnesium sulfate
  5. customChloroform was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-7e896f88740b4ab38a5d9fc963ea8aa7
Source dataset
uspto-grants-2015_02
Patent number
US08962850B2

Reaction notes

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