Glycerol → 7-Ethylquinoline

HRID 513408Notes

Reaction equation

HRID 513408 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6])[CH3:2].O[CH2:11][CH:12]([CH2:14]O)O.[Na+].[N+](C1C=C(S([O-])(=O)=O)C=CC=1)([O-])=O.OS(O)(=O)=O>O>[CH2:1]([C:3]1[CH:4]=[C:5]2[C:7]([CH:11]=[CH:12][CH:14]=[N:6]2)=[CH:8][CH:9]=1)[CH3:2]

Participants

6

Reactant 4

HCID 753GlycerolHCID 1118Sulfuric AcidHCID 114753-EthylanilineHCID 31389Sodium 3-nitrobenzenesulfonate

Product 1

HCID 243117-EthylquinolineYield 93.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a similar fashion using route 10 general procedure 20, 3-ethylaniline (1 g, 8.25 mmol), glycerol (2.35 g, 25.6 mmol), 3-nitro benzenesulfonic acid sodium salt (2.42 g, 10.7 mmol), H2SO4:H2O (3.5 ml:2.5 ml) gave the title compound (1.21 g, 93%) which was used in the next step without purification. The structure was confirmed by 1H NMR.

Sources & evidence

ORD record
ord-1c970ec965954bb593603f129cbc537b
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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