Nitric Acid → HCID 178418737, compound

HRID 389064Notes

Reaction equation

HRID 389064 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 AcidHCID 178418765HCID 178418765, compound

Product 1

HCID 178418737HCID 178418737, compound

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 7-bromoquinolin-4-ol (594 g, 2.65 mol) in propionic acid (5 L) was heated to 120° C., and nitric acid (215 mL of 16 molar (M)) was added dropwise over a period of 2.5 hours while maintaining the temperature in the range of 119° C. to 130° C. The reaction was then cooled to 60° C. and filtered to collect a solid, which was washed sequentially with water (3×500 mL), 2-propanol (500 mL), and diethyl ether (300 mL), and pulled dry with vacuum filtration to provide 447 g of 7-bromo-3-nitroquinolin-4-ol as a tan powder.

Workup

  1. temperaturewhile maintaining the temperature in the range of 119° C. to 130° C
  2. filtrationfiltered
  3. customto collect a solid, which
  4. washwas washed sequentially with water (3×500 mL), 2-propanol (500 mL), and diethyl ether (300 mL)
  5. custompulled dry with vacuum filtration

Sources & evidence

ORD record
ord-52c5f71a0f41464c9ca22e27386d604a
Source dataset
uspto-grants-2013_02
Patent number
US08378102B2

Reaction notes

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