Isoamyl Nitrite → N-Hydroxybenzimidoyl cyanide

HRID 1948541Notes

Reaction equation

HRID 1948541 reaction equation
[N:1](OCCC(C)C)=[O:2].[C:9]1([CH2:15][C:16]#[N:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+]>C(O)C.C(OCC)C>[OH:2]/[N:1]=[C:15](\[C:16]#[N:17])/[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 8053Isoamyl NitriteHCID 8794PhenylacetonitrileHCID 14798Sodium Hydroxide

Product 1

HCID 5464219N-Hydroxybenzimidoyl cyanideYield 50.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A solution of isopentyl nitrite (16.00 g, 137 mmol) in ethyl alcohol (30 mL) was added dropwise to a solution of 2-phenylacetonitrile (16 g, 137 mmol) and sodium hydroxide (5.46 g, 137 mmol) in ethyl alcohol (30 mL) at 0° C. Once the addition was complete, the mixture was allowed to warm to room temperature. After stirring for 2h, the reaction mixture was diluted with diethyl ether and the resultant solid was collected by filtration and washed with diethyl ether. The solid was vacuum dried to yield (Z)—N-hydroxybenzimidoyl cyanide (10 g, 68.9 mmol, 50.4% yield) as a light yellow solid.

Workup

  1. additionOnce the addition
  2. filtrationthe resultant solid was collected by filtration
  3. washwashed with diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-5b6cbabece4a4edd8f22e7df1b23700a
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

Loading…