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

HRID 1895778노트

반응식

HRID 1895778 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

HCID 866758631-(3-Chloroisoquinolin-6-yl)ethanone수율 89%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6897b6f68d964845a1464363acce2ce3
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513184B2

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