Isoamyl Nitrite → HCID 73884359, compound

HRID 584357Notes

Reaction equation

HRID 584357 reaction equation
[O-]CC.[Na+].[Na].[Br:6][C:7]1[CH:8]=[C:9]([CH2:13][C:14]#[N:15])[CH:10]=[CH:11][CH:12]=1.[N:16](OCCC(C)C)=[O:17]>C(O)C.C(OCC)(=O)C.CCCCCC.C(OCC)C>[Br:6][C:7]1[CH:8]=[C:9]([C:13](=[N:16][OH:17])[C:14]#[N:15])[CH:10]=[CH:11][CH:12]=1

Participants

8

Reactant 4

HCID 8053Isoamyl NitriteHCID 36023(3-Bromophenyl)acetonitrileHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 73884359HCID 73884359, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of sodium ethoxide prepared from sodium (2.51 g) and ethanol (40 ml) was added dropwise a solution of 2-(3-bromophenyl)acetonitrile (17.8 g) in ethanol (30 ml) at 0° C., and then isoamyl nitrite (18.3 ml) was added dropwise thereto. After stirring at room temperature for 18 hours, diethyl ether was added, and washed successively with 1N hydrochloric acid, an aqueous sodium bicarbonate solution, and an aqueous saturated solution of sodium chloride. The diethyl ether layer was dried (MgSO4), concentrated, and the residue was subjected to silica gel chromatography to obtain 2-(3-bromophenyl)-2-(hydroxyimino)acetonitrile (19.9 g, yield 97%) as an orange paste from an ethyl acetate-hexane (1:1, v/v)-eluted fraction. Recrystallization from ethyl acetate-hexane gave orange crystals. m.p. 91-93° C.

Workup

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

Sources & evidence

ORD record
ord-bffb47bcd9a34e6087e10f07a59fce29
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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