1-Chloro-4-nitrobenzene → 2-(4-Nitrophenyl)-2-phenylpropanenitrile

HRID 1074301Notes

Reaction equation

HRID 1074301 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[K+].[CH3:13][CH:14]([C:21]#[N:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>N1C=CC=CC=1>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([CH3:13])[C:21]#[N:22])=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 74741-Chloro-4-nitrobenzeneHCID 14797Potassium HydroxideHCID 157612-Phenylpropionitrile

Product 1

HCID 2110592-(4-Nitrophenyl)-2-phenylpropanenitrile

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
10 °C

Procedure

This compound is synthesized according to Makosza, et al with some modifications (Makosza, M., et al, Tetrahedron (1974), 30: 3723). A solution of 4-chloronitrobenzene (31.5 g, 0.2 mol) in pyridine (100 mL) is added dropwise to a vigorously stirred suspension of KOH (fine powder 70.0 g) and α-methylbenzylcyanide (26.2 g, 0.2 mol) in pyridine (150 mL), with the reaction temperature being maintained at 10° C. The reaction mixture is stirred for 24 hours at 25° C., and poured onto an excess of HCl-ice mixture. The acidic aqueous mixture is extracted with benzene, the organic phase washed with brine, dried (Na), and the benzene evaporated under vacuum. A crude product 42.5 g (84 wt %) results and is recrystallized from isopropanolpetroleum ether to give Compound 7 as white crystals,

Workup

  1. customThis compound is synthesized
  2. extractionThe acidic aqueous mixture is extracted with benzene
  3. washthe organic phase washed with brine
  4. customdried (Na)
  5. customthe benzene evaporated under vacuum
  6. customA crude product 42.5 g (84 wt %) results
  7. customis recrystallized from isopropanolpetroleum ether

Sources & evidence

ORD record
ord-a8b9c122c3464cca8de31e935cf082a3
Source dataset
uspto-grants-1990_11
Patent number
US04973734

Reaction notes

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