2,6-Dichloropyrazine → 2-Chloro-6-(quinoline-5-oxy)-pyrazine

HRID 16291Notes

Reaction equation

HRID 16291 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:19]=[CH:18][CH:17]=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[N:15]2>CCOC(C)=O.C1CCCCC1>[Cl:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([O:9][C:10]2[C:11]3[CH:12]=[CH:13][CH:14]=[N:15][C:16]=3[CH:17]=[CH:18][CH:19]=2)[N:3]=1

Participants

5

Reactant 2

HCID 785042,6-DichloropyrazineHCID 135441757Quinolin-5-ol

Product 1

HCID 593434142-Chloro-6-(quinoline-5-oxy)-pyrazineYield 61%

Reagents, catalysts & solvents 2

HCID 8078CyclohexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Using Method DD with 2,6-dichloropyrazine (250 mg, 1.69 mmol) and 5-hydroxyquinoline (270 mg, 1.49 mmol), and purification by column chromatography (AcOEt:cyclohexane, 1:1), the title compound was obtained (264 mg). Yield: 61%. 1H NMR (250 MHz, DMSO-d6) δ 7.54-7.58 (m, 2H, Harom 3+8), 7.84 (t, 1H, Harom 7, J=8.1 Hz), 8.01 (d, 1H, Harom 6, J=8.5 Hz), 8.37 (d, 1H, Harom 4, J=8.0 Hz), 8.55 (s, 1H, HPz 5), 8.73 (s, 1H, HPz 3), 8.98 (dd, 1H, Harom 2, J=1.4 Hz, J=4.0 Hz). m/z: 258.0 [(M+H)+, calcd for C13H8ClN3O 257.0].

Sources & evidence

ORD record
ord-2d7e3c529ee14fdda3a0866235c13c02
Source dataset
uspto-grants-2010_06
Patent number
US07737152B2

Reaction notes

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