Isoamyl Nitrite → 6-Methyl-2-hydroxyimino-1-indanone

HRID 1893511Notes

Reaction equation

HRID 1893511 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.Cl.O1CCOCC1.[N:19](OCCC(C)C)=[O:20]>C(O)C>[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[N:19][OH:20])[C:8]2=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8053Isoamyl NitriteHCID 27950936-Methyl-1-indanoneHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 587173366-Methyl-2-hydroxyimino-1-indanoneYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Methylindan-1-one (5.00 g, 34.2 mmol) and 4N hydrochloric acid-dioxane solution (2 ml) were added to ethanol (30 ml), isoamyl nitrite (5.1 ml, (37.6 mmol) was added under ice-cooling, and the mixture was stirred at room temperature for 3 hr. The precipitated solid was collected by filtration and washed with diisopropyl ether to give the title compound (5.36 g, yield 89%) as a pale-yellow solid.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-335ae3620b1e4d9dba89ba613478da98
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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