Azobisisobutyronitrile → 2-Bromo-2-(4-(quinolin-7-yl)phenyl)acetonitrile

HRID 1525869Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][C:18]#[N:19])=[CH:13][CH:12]=3)[CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Br:20]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:20][CH:17]([C:14]1[CH:15]=[CH:16][C:11]([C:8]2[CH:9]=[C:10]3[C:5]([CH:4]=[CH:3][CH:2]=[N:1]3)=[CH:6][CH:7]=2)=[CH:12][CH:13]=1)[C:18]#[N:19]

Participants

Conditions

Temperature: 75 °C

Procedure

A solution of 2-(4-(quinolin-7-yl)phenyl)acetonitrile (0.409 mmol) in carbon tetrachloride (2 mL) was degassed for three minutes with a stream of nitrogen. The solution was then treated with N-bromosuccinimide (0.450 mmol) and azobisisobutyronitrile (0.020 mmol). The reaction vessel was purged with nitrogen and sealed and the mixture was allowed to stir overnight in a 75° C. oil bath. The reaction mixture was then directly loading onto silica gel and concentrated in vacuo. Purification of the residue by silica gel chromatography (0-80% ethyl acetate/hexanes) afforded the title compound (30 mg, 17%). MS(ES)+ m/e 322.9/325.0 [M+H]+ (bromide isotope pattern).

Workup

customThe reaction vessel was purged with nitrogen
customsealed
concentrationconcentrated in vacuo
customPurification of the residue by silica gel chromatography (0-80% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-d19f149b01354c72ad28eb02c41bc0f3
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09084794B2

Reaction notes

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