Water → 2-phenyl-6-vinylquinolin-4(1H)-one

HRID 1360093Notes

Reaction equation

HRID 1360093 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[CH:6][C:5]2=[O:18].[CH:19]([Sn](CCCC)(CCCC)CCCC)=[CH2:20].CCOC(C)=O.O>CS(C)=O>[C:12]1([C:7]2[NH:8][C:9]3[C:4]([C:5](=[O:18])[CH:6]=2)=[CH:3][C:2]([CH:19]=[CH2:20])=[CH:11][CH:10]=3)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 81998TributylvinyltinHCID 137916446-Bromo-2-phenylquinolin-4(1H)-one

Product 1

HCID 576171082-phenyl-6-vinylquinolin-4(1H)-oneYield 97.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6-bromo-2-phenylquinolin-4(1H)-one 1 (1.5 g, 5.0 mmol) in DMSO (60 mL) was added vinyltributyl tin (1.75 mL, 6.0 mmol) and tetrakis-triphenylphosphine palladium (116 mg, 0.1 mmol). The mixture was then heated to 100° C. for 20 h, at which time, LC-MS revealed the disappearance of starting material. The reaction was then poured into a mixture of EtOAc (200 mL) and water (400 mL) which caused a grayish solid to precipitate. This solid was collected and dried under vacuum in a desiccator over night to yield 1.21 g (97% yield) of 2-phenyl-6-vinylquinolin-4(1H)-one which was pure by 1H NMR and LC-MS. 1H NMR (400 MHz, DMSO-d6) ppm: 11.75 (br s, 1H), 8.08 (s, 1H), 7.85 (m, 3H), 7.74 (d, J=8.8 Hz, 1H), 7.59 (m, 3H), 6.88 (dd, J=17.6 Hz, 10.8 Hz, 1H), 6.34 (s, 1H), 5.90 (d, J=17.6 Hz, 1H), 5.30 (d, J=10.8 Hz, 1H). LRMS (CI, [M+H]) Calc'd=248.2. found=248.2. HRMS (APCI, [M+H]+) Calc'd for C15H11BrNO: 248.1070. found: 248.1068.

Workup

  1. customto precipitate
  2. customThis solid was collected
  3. customdried under vacuum in a desiccator over night

Sources & evidence

ORD record
ord-27ff10039f6e475289e65f851aeec4ac
Source dataset
uspto-grants-2011_02
Patent number
US07879797B2

Reaction notes

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