Sodium Hydroxide → HCID 86673701, compound

HRID 2361713Notes

Reaction equation

HRID 2361713 reaction equation
O=[C:2]1[CH2:10][CH:9]2[CH2:11][C:5]3([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:6][CH:7]([CH2:12][CH:3]1[CH2:4]3)[CH2:8]2.[NH2:21][OH:22].Cl.[OH-].[Na+]>CCO.O>[OH:22][N:21]=[C:2]1[CH2:10][CH:9]2[CH2:11][C:5]3([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:6][CH:7]([CH2:12][CH:3]1[CH2:4]3)[CH2:8]2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 71038074HCID 71038074, compound

Product 1

HCID 86673701HCID 86673701, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

The mixture of ketone 1D (10 mmol), NH2OH—HCl (5 mmol), and NaOH (5 mmol) was diluted with EtOH (5 mL) and H2O (1 mL) and the reaction mixture was heated at 80° C. for 16 h. Upon cooling, the reaction mixture was extracted with DCM (10 mL×3) and the combined organic layers were dried (Na2SO4) and concentrated to provide oxime 12A in 90% yield as a solid. The material was used in the next step without further purification. Data: LC/MS (ESR) m/z 295 [M+1]+.

Workup

  1. temperatureUpon cooling
  2. extractionthe reaction mixture was extracted with DCM (10 mL×3)
  3. dry with materialthe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-09548e30794f47c8be2f3f37cba20573
Source dataset
uspto-grants-2014_04
Patent number
US08691808B2

Reaction notes

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