Glycerol → 7-Chloro-8-nitroquinoline

HRID 513393Notes

Reaction equation

HRID 513393 reaction equation
[Cl:1][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].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>>[Cl:1][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]2[C:6]([CH:13]=[CH:14][CH:16]=[N:5]2)=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 753GlycerolHCID 31389Sodium 3-nitrobenzenesulfonateHCID 1010683-Chloro-2-nitroanilineHCID 21910475Sulfuric acid hydrate (1:1)

Product 1

HCID 4597147-Chloro-8-nitroquinolineYield 40.5%

Procedure

In a similar fashion using route 10 general procedure 20, 3-chloro-2-nitroaniline (1.0 g, 5.8 mmol), glycerol (1.65 g, 18.0 mmol), 3-nitrobenzensulfonic acid sodium salt (1.66 g, 7.5 mmol) and H2SO4/H2O (12 ml, 7:5) gave the title compound (490 mg, 40%) which was used in the next step without purification.

Sources & evidence

ORD record
ord-e2f41efa84a6411fbb48bcf974d591c4
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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