4-(Trifluoromethyl)quinoline → 8-Nitro-4-trifluoromethyl-quinoline

Reaction equation

[F:1][C:2]([F:14])([F:13])[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5][CH:4]=1.OS(O)(=O)=O.[N+:20]([O-])([OH:22])=[O:21]>>[N+:20]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[N:6]=[CH:5][CH:4]=[C:3]2[C:2]([F:1])([F:13])[F:14])([O-:22])=[O:21]

Participants

Reactant 2

HCID 27778074-(Trifluoromethyl)quinoline

HCID 71777668Sulfuric acid, mixt. with nitric acid

Product 1

HCID 681832068-Nitro-4-trifluoromethyl-quinolineYield 29%

Procedure

In a similar fashion using route 11 general procedure 57, 4-trifluoromethyl-quinoline 467 (200 mg, 1.01 mmol) and H2SO4:HNO3 (2:1) gave the title compound (70 mg, 29%) which was used in the next step without further purification.

Sources & evidence

ORD record: ord-46f643e9243a4e88bc7e6d10fde5c9d0
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102688B2

Reaction notes

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