Dimethyl Sulfide → 7-(2-Oxoethyl)-4-phenylquinoline-2-carbonitrile

HRID 2422568Notes

Reaction equation

HRID 2422568 reaction equation
[O:1]=[O+][O-].[CH2:4]([C:7]1[CH:16]=[C:15]2[C:10]([C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:12][C:13]([C:17]#[N:18])=[N:14]2)=[CH:9][CH:8]=1)[CH:5]=C.CSC>C(OCC)(=O)C>[O:1]=[CH:5][CH2:4][C:7]1[CH:16]=[C:15]2[C:10]([C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:12][C:13]([C:17]#[N:18])=[N:14]2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 597748917-Allyl-4-phenylquinoline-2-carbonitrile

Product 1

HCID 597749037-(2-Oxoethyl)-4-phenylquinoline-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ozone was bubbled into a solution of 7-allyl-4-phenylquinoline-2-carbonitrile (1.5 g, 5.6 mmol) in ethyl acetate (100 mL) at −78° C. for 1.5 h. Nitrogen was then bubbled into the solution and methylsulfide (2.1 mL, 28 mmol) was added. The reaction was brought back to room temperature, stirred for 1 h and concentrated to give the title compound. MS (+ESI): 273 (M+H)+.

Workup

  1. additionwas added
  2. customwas brought back to room temperature
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d4c43e536ec84fffa466afdd82db7aee
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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