Glycerol → 6-Methoxy-8-nitroquinoline

HRID 987570Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1.O[CH2:14][CH:15]([CH2:17]O)O.[Na+].[N+](C1C=C(S([O-])(=O)=O)C=CC=1)([O-])=O.OS(O)(=O)=O>C(Cl)Cl.O>[CH3:1][O:2][C:3]1[CH:9]=[C:8]2[C:6](=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1)[N:7]=[CH:17][CH:15]=[CH:14]2

Participants

Conditions

Temperature: 45 °C

Procedure

4-Methoxy-2-nitroaniline (20.0 g, 119 mmol), 34.0 g (369 mmol) glycerol, 24.0 g (107 mmol) 3-nitrobenzensulfonic acid sodium salt, 25 mL H2O and 34 mL H2SO4 are refluxed for 12 h. The reaction mixture is cooled to 45° C., poured into 1 L of cold H2O and vigorously stirred with 500 mL of CH2Cl2 for 30 min. The resulting bi-phasic solution is filtered through celite, and the aqueous layer is extracted with 3×300 mL CH2Cl2. The combined organics are washed with 1×400 mL H2O, 1×400 mL brine, dried over MgSO4, filtered, and the volatiles are evaporated. Flash chromatography of the crude product on SiO2 gel, eluting with hexanes/EtOAc (4/1), gives 10.0 g (49.0 mmol, a 42% yield) of the title compound as a tan solid. MS (ES) m/z 205 (MH)+.

Workup

filtrationThe resulting bi-phasic solution is filtered through celite
extractionthe aqueous layer is extracted with 3×300 mL CH2Cl2
washThe combined organics are washed with 1×400 mL H2O, 1×400 mL brine
dry with materialdried over MgSO4
filtrationfiltered
customthe volatiles are evaporated
washFlash chromatography of the crude product on SiO2 gel, eluting with hexanes/EtOAc (4/1)
customgives 10.0 g (49.0 mmol

Sources & evidence

ORD record: ord-87c92e86ab7343db826afdfb83a5e7b8
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06632824B2

Reaction notes

Loading…