2-Phenylpropionitrile → HCID 12690046, compound

HRID 2077044Notes

Reaction equation

HRID 2077044 reaction equation
[Cl-].[NH4+:2].C[Al](C)C.[C:7]1([CH:13]([CH3:16])[C:14]#[N:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1(C)C=CC=CC=1.ClCCl>[C:7]1([CH:13]([CH3:16])[C:14](=[NH:2])[NH2:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 157612-PhenylpropionitrileHCID 25517Ammonium ChlorideHCID 16682925Trimethylaluminum

Product 1

HCID 12690046HCID 12690046, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Ammonium chloride (535 mg, 10.0 mmol) was suspended in toluene (3 ml), cooled to 0° C., under nitrogen then trimethylaluminium (5 ml, 2M in toluene) was added dropwise. The reaction mixture was warmed to room temperature and stirred for 2 h. Then 2-phenylpropionitrile (1.33 ml, 10.0 mmol) in toluene (2 ml) was added and heated to 80° C. for 17 h. The reaction mixture was poured onto a slurry of silica (20 g) in dichloromethane (20 ml) and stirred for 5 min. It was filtered and the filtrate concentrated in vacuo. Trituration of the residue with diethyl ether afforded the title compound as a solid in 95% yield, 1.75 g.

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. temperatureheated to 80° C. for 17 h
  3. stirringstirred for 5 min
  4. filtrationIt was filtered
  5. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-252064ab113e4a319a794dcdc8565a8b
Source dataset
uspto-grants-2011_04
Patent number
US07928099B2

Reaction notes

Loading…