Glycerol → 5-Chloro-6-fluoro-8-nitroquinoline

HRID 513394Notes

Reaction equation

HRID 513394 reaction equation
[Cl:1][C:2]1[C:3]([F:12])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].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.O>>[Cl:1][C:2]1[C:3]([F:12])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]2[C:8]=1[CH:14]=[CH:15][CH:17]=[N:7]2

Participants

5

Reactant 4

HCID 753GlycerolHCID 31389Sodium 3-nitrobenzenesulfonateHCID 5178355-Chloro-4-fluoro-2-nitroanilineHCID 21910475Sulfuric acid hydrate (1:1)

Product 1

HCID 681829415-Chloro-6-fluoro-8-nitroquinolineYield 67%

Procedure

In a similar fashion using route 10 general procedure 20, 5-chloro-4-fluoro-2-nitroaniline (1.0 g, 5.2 mmol), glycerol (1.5 g, 16.2 mmol), 3-nitrobenzensulfonic acid sodium salt (1.52 g, 6.7 mmol) and H2SO4/H2O (6 ml, 7:5) gave the title compound (790 mg, 67%) which was used in the next step without purification.

Sources & evidence

ORD record
ord-40b4953077fb488c95d4dd8894d37b78
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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