6-Hydroxyquinoline → 2-Chloro-6-(quinoline-6-oxy)-pyrazine

HRID 16292

Reaction equation

HRID 16292 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[OH:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[CH:15][CH:14]=[CH:13]2>CCOC(C)=O.C1CCCCC1>[Cl:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([O:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[CH:13]3)[N:3]=1

Participants

4

Reactant 2

HCID 113746-HydroxyquinolineHCID 785042,6-Dichloropyrazine

Product 1

HCID 593434492-Chloro-6-(quinoline-6-oxy)-pyrazineYield 75%

Reagents, catalysts & solvents 1

HCID 21867204Cyclohexane ethylacetateSolvent

Procedure

Using Method DD with 2,6-dichloropyrazine (250 mg, 1.69 mmol) and 6-hydroxyquinoline (270 mg, 1.49 mmol), and purification by column chromatography (AcOEt cyclohexane, 1:1), the title compound was obtained (324 mg). Yield: 75%. 1H NMR (250 MHz, DMSO-d6) δ 7.56-7.59 (m, 1H, Harom 3), 7.70 (dd, 1H, Harom 7, Jm=2.6 Hz, Jo=9.1 Hz), 7.87 (d, 1H, Harom 5, J=2.4 Hz), 8.12 (d, 1H, Harom 8, J=9.0 Hz), 8.37 (d, 1H, Harom 4, J=8.1 Hz), 8.56 (s, 1H, HPz 5) 8.65 (s, 1H, HPz 3), 8.93 (dd, 1H, Harom 2, J=1.0 Hz, J=4.9 Hz). m/z: 258.0 [(M+H)+, calcd for C13H8ClN3O 257.0].

Sources & evidence

ORD record
ord-984f0f2912364b4c8c9245b6aeeb3dce
Source dataset
uspto-grants-2010_06
Patent number
US07737152B2

Linked notes

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