Sodium Hydroxide → trans-2-(2-Methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropanecarbaldehyde oxime

HRID 1639756Notes

Reaction equation

HRID 1639756 reaction equation
[CH3:1][C:2]1[CH:15]=[C:5]2[C:6]([C@@H:10]3[CH2:12][C@H:11]3[CH:13]=O)=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[OH-:16].[Na+].Cl.[NH2:19]O>C(O)C.O>[CH3:1][C:2]1[CH:15]=[C:5]2[C:6]([C@@H:10]3[CH2:12][C@H:11]3[CH:13]=[N:19][OH:16])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 86641921trans-2-(2-Methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropanecarbaldehyde

Product 1

HCID 86641923trans-2-(2-Methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropanecarbaldehyde oximeYield 96%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
60 °C

Procedure

Trans-2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropanecarbaldehyde (1.62 g, 8.08 mmol), 8 M aqueous sodium hydroxide solution (4.04 mL, 32.3 mmol) and hydroxylamine hydrochloride (1.85 g, 26.7 mmol) was dissolved in ethanol/water (65 mL/13 mL), and the mixture was stirred at 60° C. for 3 hr. The reaction solution was concentrated, extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (1.67 g, yield 96%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-bcb257a54ee1455985a63694bb43bc39
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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