Glycerol → 5-Fluoro-8-nitroquinoline

HRID 513391Notes

Reaction equation

HRID 513391 reaction equation
[F: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>>[F: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

Participants

5

Reactant 4

HCID 753GlycerolHCID 31389Sodium 3-nitrobenzenesulfonateHCID 753995-Fluoro-2-nitroanilineHCID 21910475Sulfuric acid hydrate (1:1)

Product 1

HCID 1539725-Fluoro-8-nitroquinolineYield 60%

Procedure

In a similar fashion using route 10 general procedure 20, 5-fluoro-2-nitroaniline (1.0 g, 6.4 mmol), glycerol (1.83 g, 19.86 mmol), 3-nitrobenzenesulfonic acid sodium salt (1.8 g, 8.33 mmol) and H2SO4/H2O (1.2 ml, 7:5) gave the title compound (500 mg, 60%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-81664ce63b6e4ffbbcbeb00f2e00e31c
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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