HCID 10785365, compound → 4,4′-Dinitro[1,1′-biphenyl]-2-carbonitrile

HRID 1005258Notes

Reaction equation

HRID 1005258 reaction equation
I[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1.[C:20]([Cu])#[N:21]>[Cl-].[NH4+]>[C:20]([C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)#[N:21]

Participants

4

Reactant 2

HCID 10785365HCID 10785365, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 105398964,4′-Dinitro[1,1′-biphenyl]-2-carbonitrileYield 90%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

A solution of the iodide 77 (5.0 g, 13.66 mmol) and CuCN (1.65 g, 18.42 mmol) in 30 mL of anhydrous dimethiylsulfoxide was heated (180° C.) under an argon atmosphere. After 2 hr, the reaction mixture was added to a 0° solution of aqueous ammonium chloride (100 mL) and filtered through a Buchner funnel. The insoluble product was partitioned into methylene chloride and water. The separated or ganic layer was dried over MgSO4 and concentrated. The crude product was purified by silica gel chromatography (1/1 Hexane/CH2Cl2 to 30%/69%/1% Hexane(CH2Cl2 /MeOH) to afford the nitrile 78 (3.3 g, 12.27 mmol, 90% from 77) as a light yellow solid. 1H NMR (DMSO-d6) δ8.69 (d, 1H, J=2.3), 8.56 (dd, 1H, J1 =8.6, J=2.3), 8.44-8.41 (m, 2H), 7.80-7.76 (m, 3H).

Workup

  1. filtrationfiltered through a Buchner funnel
  2. customThe insoluble product was partitioned into methylene chloride and water
  3. customThe separated
  4. dry with materialganic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel chromatography (1/1 Hexane/CH2Cl2 to 30%/69%/1% Hexane(CH2Cl2 /MeOH)

Sources & evidence

ORD record
ord-fba7aa2a6e4b49a5a6fdacb2ef6fdf21
Source dataset
uspto-grants-2000_04
Patent number
US06054114

Reaction notes

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