Sulfuric Acid → 7-METHOXY-8-NITROQUINOLINE

HRID 513412Notes

Reaction equation

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

Participants

Reactant 3

HCID 1118Sulfuric Acid

HCID 24434Potassium Nitrate

HCID 786667-Methoxyquinoline2×

Product 1

HCID 112064927-METHOXY-8-NITROQUINOLINEYield 50%

Procedure

In a similar fashion using route 7 general procedure 15, 7-methoxyquinoline (Intermediate 58) (400 mg, 2.51 mmol), potassium nitrate (330 mg, 3.26 mmol) and conc. H2SO4 (1.2 ml) gave the title compound (250 mg, 50%) after purification by column chromatography with n-hexane/EtOAc (3:1) as the eluent.

Sources & evidence

ORD record: ord-ae2c31661e474a0f92222bcd3eb5f09e
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102688B2

Reaction notes

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