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

HRID 2423317

Reaction equation

HRID 2423317 reaction equation
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

Participants

4

Reactant 3

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

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-93fc0c8368b94319aaeb41600691f435
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Linked notes

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