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

HRID 2380329

Reaction equation

HRID 2380329 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-44227dcbed574b8394712fbb0dc59a15
Source dataset
uspto-grants-1994_11
Patent number
US05366982

Linked notes

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