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

HRID 1783296Notes

Reaction equation

HRID 1783296 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.[N:12](OCCC(C)C)=[O:13].Cl.O1CCOCC1>C(O)C>[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[N:12][OH:13])[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-indanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Methyl-1-indanone (40.4 g) and isoamyl nitrite (40.6 mL) were dissolved in ethanol (300 mL), and 4N hydrogen chloride-dioxane (10 mL) was added dropwise under ice-cooling. After the completion of the reaction, the precipitated crystals were collected by filtration and washed with ether to give 6-methyl-2-hydroxyimino-1-indanone (37 g).

Workup

  1. temperaturecooling
  2. customAfter the completion of the reaction
  3. filtrationthe precipitated crystals were collected by filtration
  4. washwashed with ether

Sources & evidence

ORD record
ord-7d49fe7db0444eacaa2175ac7a59ed16
Source dataset
uspto-grants-2009_03
Patent number
US07501412B2

Reaction notes

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