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Phosphorus oxychloride → 7-Chloro-3,5-dimethylisoxazolo[4,5-b]pyridine

HRID 335138
Notes
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Reaction equation

HRID 335138 reaction equation
[CH3:1][C:2]1[C:6]2=[N+:7]([O-])[C:8]([CH3:11])=[CH:9][CH:10]=[C:5]2[O:4][N:3]=1.O=P(Cl)(Cl)[Cl:15].C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[Cl:15][C:10]1[CH:9]=[C:8]([CH3:11])[N:7]=[C:6]2[C:2]([CH3:1])=[N:3][O:4][C:5]=12
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 66995125HCID 66995125, compound

Product 1

HCID 669950867-Chloro-3,5-dimethylisoxazolo[4,5-b]pyridineYield 57.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

3,5-dimethylisoxazolo[4,5-b]pyridine 4-oxide (0.650 g, 3.96 mmol) in chloroform (5 mL), was added POCl3 (1.45 mL, 15.8 mmol) and the mixture was heated at 80° C. for 2 hours. The solution was cooled and poured onto ice water. The solution was neutralized with saturated NaHCO3 and the solution was then extracted with EtOAc, dried, and concentrated. The solid was triturated with ether and filtered twice to obtain two crops of the title compound (0.417 g, 57.7% yield).

Workup

  1. temperatureThe solution was cooled
  2. additionpoured onto ice water
  3. extractionthe solution was then extracted with EtOAc
  4. customdried
  5. concentrationconcentrated
  6. customThe solid was triturated with ether
  7. filtrationfiltered twice

Sources & evidence

ORD record
ord-7c88b5edef0a471e932cb6e4166ce561
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08883828B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes