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

HRID 472156

反応式

HRID 472156 の反応式
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

参加物

7

反応物 4

HCID 795ImidazoleHCID 6049Ethylenediaminetetraacetic AcidHCID 11430Potassium CarbonateHCID 106575386-Bromo-2-methoxyquinoline

生成物 1

HCID 582704576-(1H-imidazol-1-yl)-2-methoxy-quinoline収率 78%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

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).

後処理

  1. temperatureThe reaction mixture was cooled at r.t.
  2. filtrationthe resulting precipitate was filtered
  3. washwashed with water
  4. customdried
  5. stirringThe resulting suspension was stirred for 10 min.
  6. filtrationfiltered
  7. customthe collected title product
  8. customwas dried

出典と根拠

ORDレコード
ord-eb29b799e335402d9ce131ea62e586a2
出典データセット
uspto-grants-2014_01
特許番号
US08633208B2

関連ノート

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