Glycerol → Quinoline, 6-fluoro-8-nitro-

HRID 513389Notes

Reaction equation

HRID 513389 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.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:8]=[C:7]2[C:5](=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1)[N:6]=[CH:16][CH:14]=[CH:13]2

Participants

5

Reactant 4

HCID 753GlycerolHCID 31389Sodium 3-nitrobenzenesulfonateHCID 677694-Fluoro-2-nitroanilineHCID 21910475Sulfuric acid hydrate (1:1)

Product 1

HCID 154273Quinoline, 6-fluoro-8-nitro-Yield 84.4%

Procedure

In a similar fashion using route 10 general procedure 20, 4-fluoro-2-nitroaniline (1.0 g, 6.41 mmol), glycerol (1.83 g, 19.9 mmol), 3-nitrobenzenesulfonic acid sodium salt (1.8 g, 8.33 mmol) and H2SO4/H2O (6 ml, 7:5) gave the title compound (1.04 g, 84%) which was used in the next step without purification.

Sources & evidence

ORD record
ord-01cabbe597f7482ab45b769d0e986014
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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