Ethanol → Ethyl 2-(3-methoxy-4-(5-nitroquinolin-6-yloxy)phenyl)acetate

HRID 2423317

반응식

HRID 2423317 반응식
S(=O)(=O)(O)O.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH2:28][C:29]([OH:31])=[O:30])[CH:11]=[CH:12][C:13]=1[O:14][C:15]1[C:16]([N+:25]([O-:27])=[O:26])=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2.[CH3:32][CH2:33]O>>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:11]=[CH:12][C:13]=1[O:14][C:15]1[C:16]([N+:25]([O-:27])=[O:26])=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2

참가 물질

4

반응물 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 598648342-(3-Methoxy-4-(5-nitroquinolin-6-yloxy)phenyl)acetic acid

생성물 1

HCID 59864865Ethyl 2-(3-methoxy-4-(5-nitroquinolin-6-yloxy)phenyl)acetate

실험 절차

Concentrated sulfuric acid (0.32 mL, 11.3 mmol) was added to 24.2 (4 g, 11.3 mmol) in EtOH. The mixture was heated to reflux for 15 h. After cooling, EtOH was evaporated under vacuum, and the residue was treated with EtOAc (100 mL). Saturated NaHCO3 was added to neutralize the acid. The organic layer was separated, dried with MgSO4 and concentrated to give 24.3. MS ESI (pos.) m/z: 383.1 (M+H). 1H NMR (DMSO-d6) δ 8.99 (dd, 1H); 8.24 (m, 2H); 7.77 (dd, 1H); 7.29 (d, 1H); 7.21 (d, 1H); 7.18 (d, 1H); 6.96 (dd, 1H); 4.13 (q, 2H); 3.73 (s, 5H); 1.23 (t, 3H).

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 15 h
  3. temperatureAfter cooling
  4. customEtOH was evaporated under vacuum
  5. additionthe residue was treated with EtOAc (100 mL)
  6. additionSaturated NaHCO3 was added
  7. customThe organic layer was separated
  8. dry with materialdried with MgSO4
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-93fc0c8368b94319aaeb41600691f435
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960567B2

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