6-Bromohexanenitrile → 6-[(4,6-Diphenyl-2-pyridyl)oxy]hexanonitrile

HRID 2396506Notes

Reaction equation

HRID 2396506 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:10][C:9](=[O:19])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]#[N:27]>C(=O)([O-])[O-].[Ag+2].C1(C)C=CC=CC=1>[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:10]=[C:9]([O:19][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]#[N:27])[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 810936-BromohexanenitrileHCID 38462014,6-Diphenyl-2-pyridone

Product 1

HCID 103374486-[(4,6-Diphenyl-2-pyridyl)oxy]hexanonitrile

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 1140TolueneSolvent

Procedure

The procedure of Example 4 is followed using 4,6-diphenyl-2-pyridone (6.18 g) and 6-bromohexanonitrile (6.60 g) in place of 6-bromohexanoate, silver carbonate (6.89 g) and toluene (300 cc) and the reaction mixture is refluxed for 72 hours. The material formed is purified by chromatography under pressure on silica gel (30-60 mm; eluent: n-hexane-ethyl acetate 9.5-0.5) to obtain 6-[(4,6-diphenyl-2-pyridyl)oxy]hexanonitrile as a white solid which is used directly in subsequent reactions.

Workup

  1. temperaturethe reaction mixture is refluxed for 72 hours
  2. customThe material formed
  3. customis purified by chromatography under pressure on silica gel (30-60 mm; eluent: n-hexane-ethyl acetate 9.5-0.5)

Sources & evidence

ORD record
ord-29ea385ba8bc418aa7910baadc7f5a78
Source dataset
uspto-grants-1996_02
Patent number
US05492915

Reaction notes

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