3-Chloro-6-(1-ethoxy-vinyl)-isoquinoline → 1-(3-Chloroisoquinolin-6-yl)ethanone

HRID 1895778ノート

反応式

HRID 1895778 の反応式
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([C:12]([O:14]CC)=[CH2:13])=[CH:7][CH:6]=2>O1CCOCC1.Cl>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([C:12](=[O:14])[CH3:13])=[CH:7][CH:6]=2

参加物

4

反応物 1

HCID 866758623-Chloro-6-(1-ethoxy-vinyl)-isoquinoline

生成物 1

HCID 866758631-(3-Chloroisoquinolin-6-yl)ethanone収率 89%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 312751,4-Dioxane溶媒

実験手順

A solution of 3-chloro-6-(1-ethoxy-vinyl)-isoquinoline (934 mg, 4 mmol) in 1,4-dioxane (10 mL) and hydrochloric acid (2 M, 5 mL) was stirred at room temperature for 30 minutes. The solvent was evaporated and the residue was partitioned between ethyl acetate and water. The organic extracts were combined, washed with water and brine, dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography using a gradient of iso-hexanes/ethyl acetate 9:1 to 4:1 to afford the title compound (732 mg, 89%) as a white solid. 1H NMR (300 MHz, CDCl3) δ2.77 (s, 3H), 7.88 (s, 1H), 8.05 (d, J=8.5 Hz, 1H), 8.15 (dd, J=8.5, 1.4 Hz, 1H), 8.37 (br s, H), 9.17 (s, 1H). LCMS (m/z) 206/208 [M+H], Tr=4.40 min.

後処理

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between ethyl acetate and water
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-6897b6f68d964845a1464363acce2ce3
出典データセット
uspto-grants-2013_08
特許番号
US08513184B2

反応ノート

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