Nitric Acid → 4-Chloro-8-nitroquinoline

HRID 513730Notes

Reaction equation

HRID 513730 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[N+:12]([O-])([OH:14])=[O:13].OS(O)(=O)=O>>[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 691404-Chloroquinoline

Product 1

HCID 6104404-Chloro-8-nitroquinolineYield 36%

Procedure

In a similar fashion using route 11 general procedure 57, 4-chloroquinoline 462 (5.0 g, 30.7 mmol), fuming HNO3 (8.3 ml) and concentrated H2SO4 (16.6 ml) to give the title compound (2.3 g, 36%) which was used in the next step without further purification.

Sources & evidence

ORD record
ord-f3262b3591a54fe58195fd968cc87ed5
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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