Glycerol → 5-Methyl-8-nitroquinoline

反応式

[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].O[CH2:13][CH:14]([CH2:16]O)O.[Na+].[N+](C1C=C(S([O-])(=O)=O)C=CC=1)([O-])=O.OS(O)(=O)=O.O>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]2[C:8]=1[CH:13]=[CH:14][CH:16]=[N:7]2

参加物

反応物 4

HCID 753Glycerol

HCID 113566-Nitro-m-toluidine

HCID 31389Sodium 3-nitrobenzenesulfonate

HCID 21910475Sulfuric acid hydrate (1:1)

生成物 1

HCID 64278395-Methyl-8-nitroquinoline収率 77%

反応条件

温度: 105 °C

実験手順

5-methyl-2-nitroaniline (1.0 g, 6.57 mmol), glycerol (1.88 g, 20.4 mmol), 3-nitrobenzenesulfonic acid sodium salt (1.92 g, 8.54 mmol) were added to H2SO4/H2O (6 ml, 7:5) solution and heated at 105° C. for 48 h. After completion of the reaction (monitored by LCMS), the mixture was cooled to 45° C. and poured slowly onto ice water (50 ml) and the mixture was extracted with DCM. The combined organic phases were dried (Na2SO4) and concentrated in vacuo to give the title compound (950 mg, 77%) which was used in the next step without purification.