Sodium Hydroxide → HCID 117870451, compound

HRID 512185Notes

Reaction equation

HRID 512185 reaction equation
[F:1][C:2]1([F:18])[CH2:7][CH2:6][C:5]([C:15](=O)[CH3:16])([C:8]2[CH:9]=[N:10][C:11]([CH3:14])=[N:12][CH:13]=2)[CH2:4][CH2:3]1.[NH2:19][OH:20].Cl.[OH-].[Na+]>CCO.O>[F:1][C:2]1([F:18])[CH2:7][CH2:6][C:5](/[C:15](=[N:19]\[OH:20])/[CH3:16])([C:8]2[CH:9]=[N:10][C:11]([CH3:14])=[N:12][CH:13]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 86716212HCID 86716212, compound

Product 1

HCID 117870451HCID 117870451, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-(4,4-difluoro-1-(2-methylpyrimidin-5-yl)cyclohexyl)ethanone (350 mg, 1.38 mmol), NH2OH.HCl (143.7 mg, 2.07 mmol) and NaOH (165.6 mg, 4.14 mmol) in EtOH/H2O (16 mL, 1:1) was heated to 80° C. overnight. The EtOH was removed. The residue was extracted with EtOAc (2×20 mL). The organic layer was dried over Na2SO4 and concentrated to give (Z)-1-(4,4-difluoro-1-(2-methylpyrimidin-5-yl)cyclohexyl)ethanone oxime (320 mg), which was used for the next step directly.

Workup

  1. customThe EtOH was removed
  2. extractionThe residue was extracted with EtOAc (2×20 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-589d8fbf33d7433292a459b6e31ecb6c
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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