Sodium Hydroxide → trans-2-(2-methyl-2H-indazol-4-yl)cyclopropanecarbaldehyde oxime

HRID 1639755Notes

Reaction equation

HRID 1639755 reaction equation
[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][CH:7]=[C:8]2[C@@H:11]2[CH2:13][C@H:12]2[CH:14]=O)=[N:3]1.[OH-:16].[Na+].Cl.[NH2:19]O>C(O)C.O>[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][CH:7]=[C:8]2[C@@H:11]2[CH2:13][C@H:12]2[CH:14]=[N:19][OH:16])=[N:3]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 86641920trans-2-(2-methyl-2H-indazol-4-yl)cyclopropanecarbaldehyde

Product 1

HCID 86641922trans-2-(2-methyl-2H-indazol-4-yl)cyclopropanecarbaldehyde oximeYield 98.3%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
60 °C

Procedure

Trans-2-(2-methyl-2H-indazol-4-yl)cyclopropanecarbaldehyde (330 mg, 1.65 mmol), 8 M aqueous sodium hydroxide solution (824 μL, 6.59 mmol) and hydroxylamine hydrochloride (378 mg, 5.44 mmol) were dissolved in ethanol/water (15 mL/3 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 (349 mg, yield 98%).

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-967d83feb3834e60b42f321216201b05
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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