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

HRID 1986973Notes

Reaction equation

HRID 1986973 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:8](=[O:12])[CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)#[CH:14]>C(N(CC)CC)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:15]1([C:13]#[C:14][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:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 10821PhenylacetyleneHCID 5928392-Chloro-5,6,7,8-tetrahydroquinolin-5-one

Product 1

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

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Procedure

To a solution of 2-chloro-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-ae144a03e5144d1ba0ba8b753c2eade8
Source dataset
uspto-grants-2009_06
Patent number
US07550482B2

Reaction notes

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