2-Chloroquinoline → 2-(4-Phenylbut-1-ynyl)quinoline

HRID 422258Notes

Reaction equation

Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:12]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:13][C:14]#[CH:15]>>[C:16]1([CH2:12][CH2:13][C:14]#[C:15][C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Reactant 2

HCID 119282-Chloroquinoline

HCID 1233604-Phenyl-1-butyne

Product 1

HCID 115940802-(4-Phenylbut-1-ynyl)quinolineYield 37%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-chloroquinoline (300 mg, 1.83 mmol) and 1-(but-3-ynyl)benzene (200 mg, 1.54 mmol). The crude residue was purified by flash chromatography (cyclohexane/AcOEt 95:5) to yield 148 mg (0.57 mmol, 37%) of 2-(4-phenylbut-1-ynyl)quinoline as an orange oil.

Workup

customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 95:5)

Sources & evidence

ORD record: ord-737062e8c1b64b1cbcc1308f27196f35
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101637B2

Reaction notes

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