Sulfuric Acid → 7-Isopropyl-8-nitroquinoline

Reaction equation

[CH:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[N+:14]([O-])([O-:16])=[O:15].[K+].OS(O)(=O)=O>>[CH:1]([C:4]1[C:13]([N+:14]([O-:16])=[O:15])=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 1118Sulfuric Acid

HCID 24434Potassium Nitrate

HCID 2056289774525-47-62×

Product 1

HCID 681834287-Isopropyl-8-nitroquinolineYield 39%

Procedure

In a similar fashion using route 7 general procedure 15, 7-isopropylquinoline (Intermediate 56) (1.36 g, 7.94 mmol), potassium nitrate (1.04 g, 10.3 mmol) and H2SO4 (4.2 ml) gave the title compound (670 mg, 39%) after purification by column chromatography with n-hexane/EtOAc (9:1-22:3) as the eluent.

Sources & evidence

ORD record: ord-d3330f36e4ec48bfaba9cdf5a3641a98
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102688B2

Reaction notes

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