Nitric Acid → 4-Chloro-8-nitroquinoline

HRID 1469733Notes

Reaction equation

HRID 1469733 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 2

HCID 944Nitric AcidHCID 691404-Chloroquinoline

Product 1

HCID 6104404-Chloro-8-nitroquinoline

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
7.5 °C

Procedure

To a solution of 4-chloroquinoline (1.0 g, 6.13 mmol) in conc. H2SO4 (4.5 mL) was drop wise added conc. HNO3 (1.8 mL) at 0° C. and the reaction mixture was stirred at 0-15° C. for 3 h. Then the reaction mixture was quenched by addition of aq. NH4OH at 0° C. and the pH of the reaction mixture was adjusted to 8. The solid precipitate was filtered and the filter cake was further purified by column chromatography to afford 900 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.98 (d, J=5.1 Hz, 1H), 8.50-8.47 (d, J=9.0 Hz, 1H), 8.41 (d, J=7.8 Hz, 1H), 8.02-7.99 (d, J=4.8 Hz, 1H), 7.96-7.90 (t, J=7.8 Hz, 1H).

Workup

  1. customat 0° C.
  2. customThen the reaction mixture was quenched by addition of aq. NH4OH at 0° C.
  3. filtrationThe solid precipitate was filtered
  4. customthe filter cake was further purified by column chromatography

Sources & evidence

ORD record
ord-8b53e2aaaefe4ddaa0f535db15ad5ee5
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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