Phenylacetylene → 2-(Phenylethynyl)-7,8-dihydroquinolin-5(6H)-one

HRID 1817824Notes

Reaction equation

HRID 1817824 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:8](=[O:12])[CH2:7][C:6](C)(C)[CH2:5][C:4]=2[N:3]=1.[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)#[CH:16]>C(N(CC)CC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:17]1([C:15]#[C:16][C:2]2[CH:11]=[CH:10][C:9]3[C:8](=[O:12])[CH2:7][CH2:6][CH2:5][C:4]=3[N:3]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 10821PhenylacetyleneHCID 148125452-Chloro-7,7-dimethyl-7,8-dihydroquinolin-5(6H)-one

Product 1

HCID 113796262-(Phenylethynyl)-7,8-dihydroquinolin-5(6H)-oneYield 15%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

To a solution of 2-chloro-7,7-dimethyl-7,8-dihydro-6H-quinolin-5-one (0.2 g, 1.1 mmol) and ethynylbenzene (0.17 g, 1.6 mmol) in triethylamine (7 ml) under an argon atmosphere was added tetrakis(triphenylphosphine)palladium (0.02 g, 0.062 mmol). The mixture was heated at reflux for 3 h. Then it was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel to give the title compound (0.04 g, 15%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 h
  3. concentrationThen it was concentrated under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-93134108c8894016bbc98017da9a370d
Source dataset
uspto-grants-2009_10
Patent number
US07598384B2

Reaction notes

Loading…