2,6-Dichloropyrazine → 2-Chloro-6-(quinoline-4-oxy)-pyrazine

HRID 16290

Reaction equation

HRID 16290 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[OH:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=[CH:12][CH:11]=1>CCOC(C)=O.C1CCCCC1>[Cl:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([O:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[CH:12][CH:11]=2)[N:3]=1

Participants

4

Reactant 2

HCID 785042,6-DichloropyrazineHCID 178516385quinolin-4-ol

Product 1

HCID 593434942-Chloro-6-(quinoline-4-oxy)-pyrazineYield 14%

Reagents, catalysts & solvents 1

HCID 21867204Cyclohexane ethylacetateSolvent

Procedure

Using Method DD with 2,6-dichloropyrazine (250 mg, 1.69 mmol) and 4-hydroxyquinoline (270 mg, 1.49 mmol), and purification by column chromatography (AcOEt cyclohexane, 1:1), the title compound was obtained (60 mg). Yield: 14%. 1H NMR (250 MHz, DMSO-d6) δ 7.45 (d, 1H, Harom 3, J=4.9 Hz), 7.67 (t, 1H, Harom 7, J=7.6 Hz), 7.86 (t, 1H, Harom 6, J=7.8 Hz), 8.12 (d, 2H, Harom 3+5, J=8.7 Hz), 8.67 (s, 1H, HPz 5), 8.82 (s, 1H, HPz 3), 8.94 (d, 1H, Harom 2, J=4.9 Hz). m/z: 258.0 [(M+H)+, calcd for C13H8ClN3O 257.0].

Sources & evidence

ORD record
ord-aa8c00f800d147cb83b7d73de4a98096
Source dataset
uspto-grants-2010_06
Patent number
US07737152B2

Linked notes

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