O-Methylhydroxylamine hydrochloride → 5-tert-butyl-1-indanone O-methyloxime

HRID 656422Notes

Reaction equation

HRID 656422 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=O)[CH2:9][CH2:8]2)([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:16][O:17][NH2:18]>N1C=CC=CC=1>[CH3:16][O:17][N:18]=[C:10]1[C:11]2[C:7](=[CH:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:13][CH:12]=2)[CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 110305765-Tert-butyl-2,3-dihydroinden-1-one

Product 1

HCID 730474605-tert-butyl-1-indanone O-methyloxime

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-tert-Butyl-1-indanone (13.41 g, 71.23 mmol) and methoxyamine hydrochloride (6.68 g, 80 mmol) were dissolved in pyridine (75 ml) and stirred at ambient temperature for 16 hours. The mixture was evaporated under reduced pressure and the residue was partitioned between water and diethyl ether (X2). The combined organic layers were washed with 1N aqueous hydrochloric acid, dried with magnesium sulfate, and the filtrate was evaporated under reduced pressure to provide the title compound which was used without further purification in the next step.

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. customthe residue was partitioned between water and diethyl ether (X2)
  3. washThe combined organic layers were washed with 1N aqueous hydrochloric acid
  4. dry with materialdried with magnesium sulfate
  5. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c6296e0418874a9aa0be690b1613d277
Source dataset
uspto-grants-2011_12
Patent number
US08071762B2

Reaction notes

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