Imidazole → 6-(1H-imidazol-1-yl)-2-methoxy-quinoline

HRID 472156

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][CH3:13])[CH:6]=[CH:5]2.[NH:14]1[CH:18]=[CH:17][N:16]=[CH:15]1.C([O-])([O-])=O.[K+].[K+].C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O>CN(C=O)C.[Cu]I>[N:14]1([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[C:7]([O:12][CH3:13])[CH:6]=[CH:5]3)[CH:18]=[CH:17][N:16]=[CH:15]1

Participants

Conditions

Temperature: 150 °C

Procedure

6-bromo-2-methoxy-quinoline (19 g; 79.8 mmol; RN: 99455-05-7) was dissolved in dry DMF (100 mL), imidazole (5.7 g; 84 mmol), K2CO3 (11.6 g, 84 mmol), and CuI (1.1 g, 4.2 mmol) were added at r.t. under stirring and in argon atmosphere. The resulting mixture was heated at 150° C. for 48 hours. The reaction mixture was cooled at r.t. and poured into 2% (w/w) aqueous EDTA solution (600 mL), the resulting precipitate was filtered and washed with water, dried and then suspended in hexane/AcOEt. The resulting suspension was stirred for 10 min., filtered and the collected title product was dried, 14 g (yield 78%) of white crystals were obtained. C13H11N3O, MW: 225.25. MS (ESI) m/z: 226 (M+1). 1H-NMR (200 MHz, CDCl3) ppm: 3.6 (s, 3H), 6.97 (s, 1H), 7.51 (s, 1H), 7.82 (d, 1H), 8.10 (dd, 1H), 8.13 (d, 1H), 8.27 (s, 1H), 8.84 (d, 1H).

Workup

temperatureThe reaction mixture was cooled at r.t.
filtrationthe resulting precipitate was filtered
washwashed with water
customdried
stirringThe resulting suspension was stirred for 10 min.
filtrationfiltered
customthe collected title product
customwas dried

Sources & evidence

ORD record: ord-eb29b799e335402d9ce131ea62e586a2
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633208B2

Linked notes

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