Sulfuric Acid → 5-Bromo-8-nitroquinoline

HRID 513736Notes

Reaction equation

HRID 513736 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[Br:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][CH:11]=[N:12]2.OS(O)(=O)=O>>[Br:6][C:7]1[CH:16]=[CH:15][C:14]([N+:1]([O-:4])=[O:2])=[C:13]2[C:8]=1[CH:9]=[CH:10][CH:11]=[N:12]2

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 24434Potassium NitrateHCID 8173215-Bromoquinoline

Product 1

HCID 5816185-Bromo-8-nitroquinolineYield 92.2%

Procedure

KNO3 (1.58 g, 15.6 mmol) was added portionwise to a solution of 5-bromoquinoline (2.0 g, 12.0 mmol) conc.H2SO4 (7.5 ml) at 0° C. and the mixture was stirred at room temperature for 16 h. The mixture was poured onto ice and the resulting solid was extracted into DCM. The organic phase was washed with brine, dried (Na2SO4) and concentrated in vacuo to give the title compound (2.8 g, 92%) which was used in the next step without further purification.

Workup

  1. additionThe mixture was poured onto ice
  2. extractionthe resulting solid was extracted into DCM
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa03e42816884cf8abb18e9940d8fa0b
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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