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Acetic Acid → 2-(4-Chloro-phenyl)-3-cyclopropylmethoxy-pyridine 1-oxide

HRID 1025967
Notes
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Reaction equation

HRID 1025967 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([O:14][CH2:15][CH:16]3[CH2:18][CH2:17]3)=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.C(O)(=[O:21])C>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([O:14][CH2:15][CH:16]3[CH2:17][CH2:18]3)=[CH:12][CH:11]=[CH:10][N+:9]=2[O-:21])=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 666786972-(4-Chloro-phenyl)-3-cyclopropylmethoxy-pyridine

Product 1

HCID 666786042-(4-Chloro-phenyl)-3-cyclopropylmethoxy-pyridine 1-oxideYield 65.19%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

To a solution of 5 g 2-(4-chloro-phenyl)-3-cyclopropylmethoxy-pyridine in 15 mL acetic acid, 3 mL hydrogenperoxyde (30% in water) was added. The reaction mixture was then stirred at 70° C. for 15 h. The reaction mixture was diluted with water and quenched with sodium carbonate. The mixture was washed with methylene chloride. The organic phase was washed with water; then dried over MgSO4 and purified by chromatography on silica gel with a gradient of ethyl acetate to ethyl acetate:methanol 4:1 to yield 3.46 g (65.19%) of the title compound as white solid, MS 276.1 (M+H)+.

Workup

  1. customquenched with sodium carbonate
  2. washThe mixture was washed with methylene chloride
  3. washThe organic phase was washed with water
  4. dry with materialthen dried over MgSO4
  5. custompurified by chromatography on silica gel with a gradient of ethyl acetate to ethyl acetate:methanol 4:1

Sources & evidence

ORD record
ord-c35586a2cd5443ed9defee5c711ad146
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08729105B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes