Isoamyl Nitrite → N-Hydroxybenzimidoyl cyanide

HRID 1506508Notes

Reaction equation

HRID 1506508 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+]>CCO.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 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of isopentyl nitrite (16.00 g, 137 mmol) in EtOH (30 mL) was added dropwise to a solution of 2-phenylacetonitrile (16 g, 137 mmol) and sodium hydroxide (5.46 g, 137 mmol) while cooling in an ice bath. Once the addition was complete, the mixture was allowed to warm to room temperature. After stirring at room temperature for 2 h, the reaction was diluted with diethyl ether. The resultant precipitate was filtered and washed with diethyl ether. The solid was air dried and then vacuum dried to yield the titled compound (10 g, 68.9 mmol, 50.4% yield) as a light yellow solid.

Workup

  1. temperaturewhile cooling in an ice bath
  2. additionOnce the addition
  3. filtrationThe resultant precipitate was filtered
  4. washwashed with diethyl ether
  5. customdried
  6. customvacuum dried

Sources & evidence

ORD record
ord-1655d6393ddd41f7a76c1b99bd24cc5d
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

Loading…