Sodium Hydroxide → 3-Methylindan-1-one oxime

HRID 1747572

Reaction equation

HRID 1747572 reaction equation
[CH3:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=O)[CH2:3]1.Cl.[NH2:13][OH:14].[OH-].[Na+]>CO.O>[CH3:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[N:13][OH:14])[CH2:3]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 2595603-Methyl-indan-1-oneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 28186713-Methylindan-1-one oxime

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-methylindan-1-one (221 mg, 1.51 mmol) and hydroxylamine hydrochloride (295 mg, 4.25 mmol) in MeOH (4.00 mL) was added a solution of NaOH (200 mg, 5.00 mmol) in H2O (2.00 mL) and the mixture was stirred at 80° C. for 2 h. The cooled reaction was concentrated in vacuo to remove most of the MeOH, and the residue was partitioned between DCM and H2O. The organic layer was concentrated in vacuo to afford the title compound as a waxy solid (232 mg, 95%). LC/MS: Rt=1.51 min, ES+ 162 (AA standard).

Workup

  1. customThe cooled reaction
  2. concentrationwas concentrated in vacuo
  3. customto remove most of the MeOH
  4. customthe residue was partitioned between DCM and H2O
  5. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-7468c53210a34c6dae166050425fcda4
Source dataset
uspto-grants-2015_10
Patent number
US09150525B2

Linked notes

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