Water → HCID 16643583, compound

HRID 423103Notes

Reaction equation

HRID 423103 reaction equation
CO/[N:3]=[C:4](\[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)/[CH2:5][N:6]1[CH:10]=[CH:9][CH:8]=[N:7]1.O.[OH-].[Na+].C(OCC)C>C1COCC1>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([CH:4]([NH2:3])[CH2:5][N:6]2[CH:10]=[CH:9][CH:8]=[N:7]2)=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 57750295(E)-1-(4-chlorophenyl)-N-methoxy-2-pyrazol-1-ylethanimine3×

Product 1

HCID 16643583HCID 16643583, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane tetrahydrofuran complex (15.00 mL, 15.00 mmol) was added to a stirred solution of (Z) and (E)-1-(4-chlorophenyl)-2-(1H-pyrazol-1-yl)ethanone O-methyl oxime (Intermediate 91) (0.749 g, 3 mmol) dissolved in THF (30 mL) at room temperature under argon. The resulting solution was stirred under reflux for 3 hours. The mixture was cooled in an ice/water bath and water (25 ml) was carefully added followed by 20% NaOH (25 ml). The resulting biphasic mixture was refluxed overnight with vigorous magnetic stirring and allowed to cool. Diethyl ether was added and the layers were separated. The organic layer was further extracted with diethyl ether dried over MgSO4, filtered and evaporated to give the crude product (741 mg, 55%). This was used directly in the following reaction.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureThe mixture was cooled in an ice/water bath
  3. temperatureThe resulting biphasic mixture was refluxed overnight with vigorous
  4. stirringmagnetic stirring
  5. temperatureto cool
  6. customthe layers were separated
  7. extractionThe organic layer was further extracted with diethyl ether
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-b8970c45f9ad400aa664dea73f5cbec4
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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