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Sodium Hydroxide → 3-Chloro-5-(1,3-dioxolan-2-yl)-2-methylpyridine 1-oxide

HRID 420726
Notes
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Reaction equation

HRID 420726 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[C:14]([CH3:24])=[N:15][CH:16]=[C:17]([CH:19]2[O:23][CH2:22][CH2:21][O:20]2)[CH:18]=1.C([O-])(O)=O.[Na+].[OH-].[Na+]>C(Cl)Cl>[Cl:12][C:13]1[C:14]([CH3:24])=[N+:15]([O-:9])[CH:16]=[C:17]([CH:19]2[O:23][CH2:22][CH2:21][O:20]2)[CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 66658303HCID 66658303, compound

Product 1

HCID 666582803-Chloro-5-(1,3-dioxolan-2-yl)-2-methylpyridine 1-oxideYield 78%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

m-CPBA (626 mg, 2.72 mmol) was added to a suspension of 3-chloro-5-(1,3-dioxolan-2-yl)-2-methylpyridine (271.4 mg, 1.359 mmol) and NaHCO3 (343 mg, 4.08 mmol) in DCM (3 ml) and stirred at room temperature. After 21 h, HPLC showed full conversion. DCM and 1M NaOH were added. It was extracted, dried (MgSO4), filtered, and concentrated yielding 3-chloro-5-(1,3-dioxolan-2-yl)-2-methylpyridine 1-oxide (228 mg, 78%) as a pale yellow oil pure enough to be used in the next step.

Workup

  1. extractionIt was extracted
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8a5616c5182b4f38aafb4d5f3b7fee24
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08097628B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes