Sulfuric Acid → 5-Chloro-8-nitroquinoline

HRID 513378Notes

Reaction equation

HRID 513378 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[N+:12]([O-])([O-:14])=[O:13].[K+].OS(O)(=O)=O>C(Cl)Cl.CCCCC>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 24434Potassium NitrateHCID 694585-Chloroquinoline

Product 1

HCID 2427555-Chloro-8-nitroquinolineYield 51%

Reagents, catalysts & solvents 1

HCID 21877063Dichloromethane pentaneSolvent

Procedure

In a similar fashion using route 7 general procedure 15, 5-chloroquinoline (1.0 g, 6.13 mmol), potassium nitrate (0.8 g, 7.98 mmol) and H2SO4 (3 ml) gave the title compound (630 mg, 51%) after trituration from DCM/n-pentane.

Sources & evidence

ORD record
ord-db14921b42524c4eb26cb62c4f69a82d
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…