Potassium Carbonate → 1-Chloro-4-ethoxyisoquinoline

HRID 1852223ノート

反応式

HRID 1852223 の反応式
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](F)[CH:10]=2)[C:5]([OH:13])=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].[CH:20]1(CBr)C[CH2:21]1>C(#N)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:13][CH2:20][CH3:21])=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 717427161-Chloro-7-fluoroisoquinolin-4-OL

生成物 1

HCID 866832431-Chloro-4-ethoxyisoquinoline収率 66.6%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
50 °C

実験手順

To a solution of 1-chloro-7-fluoro-4-hydroxyisoquinoline (1.0 g, 5.06 mmol) in acetonitrile (10 ml) was added K2CO3 (2 g, 15.18 mmol) followed by cyclopropylmethylbromide (1.36 g, 10.12 mmol) at room temperature. The reaction mixture was heated to 50° C. for 2 hr. Solvent was evaporated under reduced pressure and the residue was diluted with water and extracted with ethyl acetate. The combined organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to get 1-chloro-4-ethoxyisoquinoline (0.7 g, 55%) as pale yellow solid. 1H NMR (400 MHz, CDCl3): δ ppm 8.38-8.34 (q, J=8 Hz, 1H), 7.89-7.86 (d, J=12 Hz, 1H), 7.81 (s, 1H), 7.65 (t, J=10 Hz, 1H), 4.11-4.09 (d, J=8 Hz, 2H), 1.43-1.37 (m, 1H), 0.72-0.67 (m, 2H), 0.46-0.39 (m, 2H); MS: MS m/z 252.0 (M++1).

後処理

  1. customSolvent was evaporated under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  5. customevaporated under reduced pressure
  6. customto get crude compound
  7. customThe crude compound was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-120dcf58922247a3b836d29c2aba88b7
出典データセット
uspto-grants-2015_02
特許番号
US08957203B2

反応ノート

読み込み中…