Diphenylacetonitrile → HCID 10925096, compound

HRID 736363Notes

Reaction equation

HRID 736363 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11]1([CH:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:18]#[N:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+]>C1(C)C=CC=CC=1.CCCCCC.CCOC(C)=O>[C:20]1([C:17]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)([C:18]#[N:19])[C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 6837DiphenylacetonitrileHCID 14798Sodium HydroxideHCID 783082-Chloro-5-nitropyridineHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 10925096HCID 10925096, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a mixture of 1.0 g 2-chloro-5-nitropyridine (6.3 mmol), 1.33 g diphenylacetonitrile (6.9 mmol, 1.1 equiv) and 700 mg tetrabutylammonium fluoride (3.15 mmol, 0.5 equiv) in 3 mL toluene was added dropwise 1.5 mL 50% aqueous NaOH. After 30 min, no starting materials remained by TLC (hexane/EtOAc). The mixture was filtered through a short plug of silica to remove tars, evaporated and chromatographed (SiO2; hexane/EtOAc). The crude product was a slightly yellow oil which was recrystallized from MeOH to furnish the title compound (1.7 g, 86%) as colorless plates. mp 94-9° C. 1H NMR (CDCl3; 300 MHz) 7.20-7.29 (5H, m), 7.35-7.42 (5H, m), 7.54 (1H, d, J=8.7 Hz, H-3), 8.49 (1H, dd, J=3 and 9 Hz, H-4), 9.60 (1H, d, J=2.4 Hz, H-6). 13C NMR (CDCl3; 300 MHz) 60.19, 121.65, 123.77, 128.87, 129.09, 129.33, 132.52, 138.46, 143.49, 145.31, 164.99. Elemental analysis calculated for C19H13N3O2: C, 72.38; H, 4.13; N, 13.33. Found: C, 72.35; H, 4.08; N, 13.25.

Workup

  1. filtrationThe mixture was filtered through a short plug of silica
  2. customto remove tars
  3. customevaporated
  4. customchromatographed (SiO2; hexane/EtOAc)
  5. customwas recrystallized from MeOH

Sources & evidence

ORD record
ord-3564eeb62b1f416181bbd1dc979a9bc3
Source dataset
uspto-grants-2009_09
Patent number
US07595331B2

Reaction notes

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