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

HRID 1881726
Notes
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Reaction equation

HRID 1881726 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-e319aa7780f649db8974a32dd5315873
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08318940B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes