Isoamyl Nitrite → 2-(3-Benzoylphenyl)-2-(hydroxyimino)acetonitrile

HRID 584358Notes

Reaction equation

HRID 584358 reaction equation
[O-]CC.[Na+].[Na].[C:6]([C:14]1[CH:15]=[C:16]([CH2:20][C:21]#[N:22])[CH:17]=[CH:18][CH:19]=1)(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[N:23](OCCC(C)C)=[O:24]>C(O)C.C(OCC)(=O)C>[C:6]([C:14]1[CH:15]=[C:16]([C:20](=[N:23][OH:24])[C:21]#[N:22])[CH:17]=[CH:18][CH:19]=1)(=[O:13])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 8053Isoamyl NitriteHCID 88857(3-Benzoylphenyl)ethanenitrileHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 738843482-(3-Benzoylphenyl)-2-(hydroxyimino)acetonitrileYield 99%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of sodium ethoxide prepared from sodium (1.70 g) and ethanol (40 ml) was added dropwise a solution of 2-(3-benzoylphenyl)acetonitrile (13.6 g) in ethanol (30 ml) at 0° C., and then isoamyl nitrite (12.4 ml) was added dropwise. After stirring at room temperature for 15 hours, the reaction mixture was diluted with ethyl acetate and washed successively with 1N hydrochloric acid and an aqueous saturated solution of sodium chloride. The ethyl acetate layer was dried (MgSO4) and concentrated to obtain 2-(3-benzoylphenyl)-2-(hydroxyimino)acetonitrile (15.2 g, yield 99%) as crystals. Recrystallization from ethyl acetate-hexane gave an isomer of 2-(3-benzoylphenyl)-2-(hydroxyimino)acetonitrile as colorless crystals. m.p. 175-176° C.

Workup

  1. washwashed successively with 1N hydrochloric acid
  2. dry with materialThe ethyl acetate layer was dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-995be27a0d574b37a015513293415fef
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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