Nitric Acid → HCID 178418737, compound

HRID 1907968Notes

Reaction equation

HRID 1907968 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:12])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[N+:13]([O-])([OH:15])=[O:14]>C(O)(=O)CC>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:12])=[C:7]([N+:13]([O-:15])=[O:14])[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 944Nitric Acid2×HCID 178418765HCID 178418765, compound

Product 1

HCID 178418737HCID 178418737, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent2×

Conditions

Temperature
112.5 °C

Procedure

A stirred suspension of 7-bromoquinolin-4-ol (162 g, 0.723 mol) in propionic acid (1500 mL) was brought to 110° C. Nitric acid (85 g of 70%) was added dropwise over 1 hour such that the temperature was maintained between 110-115° C. After half of the nitric acid had been added, stirring became difficult due to the formation of solids and an additional 200 mL of propionic acid was added. Upon complete addition, the reaction was stirred for 1 hour at 110° C., cooled to room temperature, and the solid was collected by filtration. The filter cake was washed with ice cold ethanol until the washings were nearly colorless (800 mL), and the product was dried at 60° C. under vacuum to afford 152 g of 7-bromo-3-nitro-quinolin-4-ol as a pale yellow solid.

Workup

  1. customwas brought to 110° C
  2. additionUpon complete addition
  3. stirringthe reaction was stirred for 1 hour at 110° C.
  4. temperaturecooled to room temperature
  5. filtrationthe solid was collected by filtration
  6. washThe filter cake was washed with ice cold ethanol until the washings
  7. customthe product was dried at 60° C. under vacuum

Sources & evidence

ORD record
ord-fd0d5cd8c620432581ac573f4b525c27
Source dataset
uspto-grants-2013_12
Patent number
US08598192B2

Reaction notes

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