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

反応式

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

参加物

反応物 3

HCID 702Ethanol

HCID 1118Sulfuric Acid

HCID 598648342-(3-Methoxy-4-(5-nitroquinolin-6-yloxy)phenyl)acetic acid

生成物 1

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

実験手順

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).