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

HRID 472156

반응식

HRID 472156 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

반응 조건

온도
150 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-eb29b799e335402d9ce131ea62e586a2
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633208B2

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