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

HRID 1821607Notes

Reaction equation

HRID 1821607 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 56.3%

Conditions

Temperature
115 °C

Procedure

Solid pyrazole (3.2 g, 47.36 mmol, 3.0 equiv.) was heated and melted at 80° C. Then solid 2,4-Dichloro-7-methoxy-quinoline (3.6 g, 15.78 mmol, 1.0 equiv.) was added and the mixture was then heated to 115° C. fo 3 h. Then the mixture was cooled to rt and purified by flash chromatography (20% ethyl acetate/hexane) to give 4-Chloro-7-methoxy-2-pyrazol-1-yl-quinoline (2.3 g, 8.88 mmol, 56% yield) as white solid. 1H NMR (CDCl3): 8.77 (d, 1 H, J=2.8 Hz); 8.18 (s, 1H); 8.10 (d, 1 H, J=9.2 Hz); 7.79 (s, 1H); 7.38 (d, 1 H, J=2.8 Hz); 7.23 (dd, 1 H, J=2.0, 8.8 Hz); 6.53-6.52 (m, 1H); 3.98 (s, 3H). MS m/z 260 (M++H).

Workup

  1. temperatureThen the mixture was cooled to rt
  2. custompurified by flash chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8cf46beb72c547dcb3c22870d6cd260c
Source dataset
uspto-grants-2009_10
Patent number
US07608592B2

Reaction notes

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