Pyrazole → 4-Chloro-7-methoxy-2-(1H-pyrazol-1-yl)quinoline

HRID 1852282Notes

Reaction equation

HRID 1852282 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.Cl[C:7]1[CH:16]=[C:15]([Cl:17])[C:14]2[C:9](=[CH:10][C:11]([O:18][CH3:19])=[CH:12][CH:13]=2)[N:8]=1>>[Cl:17][C:15]1[C:14]2[C:9](=[CH:10][C:11]([O:18][CH3:19])=[CH:12][CH:13]=2)[N:8]=[C:7]([N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)[CH:16]=1

Participants

3

Reactant 2

HCID 1048PyrazoleHCID 228320542,4-Dichloro-7-methoxyquinoline

Product 1

HCID 574451844-Chloro-7-methoxy-2-(1H-pyrazol-1-yl)quinolineYield 56.1%

Conditions

Temperature
115 °C

Procedure

Solid pyrazole (3.2 g, 47.36 mmol) was heated to 80° C. Then 2,4-Dichloro-7-methoxyquinoline (3.6 g, 15.78 mmol) was added. The reaction mass was heated to 115° C. for 3 hr. The reaction mass was cooled to RT and was purified by silica gel chromatography (20% ethyl acetate in pet ether) to get desired compound (2.3 g, 56%) as white solid.

Workup

  1. temperatureThe reaction mass was cooled to RT
  2. customwas purified by silica gel chromatography (20% ethyl acetate in pet ether)

Sources & evidence

ORD record
ord-13b2b7554f17433799f960915074c5f4
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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