Bromine → 5-Bromo-8-hydroxyquinoline-7-carboxylic acid

HRID 1025541Notes

Reaction equation

HRID 1025541 reaction equation
[Br:1]Br.[OH:3][C:4]1[C:5]([C:14]([OH:16])=[O:15])=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2>C(O)(=O)C>[Br:1][C:7]1[CH:6]=[C:5]([C:14]([OH:16])=[O:15])[C:4]([OH:3])=[C:13]2[C:8]=1[CH:9]=[CH:10][CH:11]=[N:12]2

Participants

4

Reactant 2

HCID 24408BromineHCID 2313638-Hydroxyquinoline-7-carboxylic Acid

Product 1

HCID 145347685-Bromo-8-hydroxyquinoline-7-carboxylic acidYield 87.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

Bromine (819.8 mg, 5.13 mmol) was added dropwise to a suspension of 8-hydroxyquinolin-7-carboxylic acid (970 mg, 5.13 mmol) in glacial acetic acid (24 mL). The reaction mixture was refluxed for 1 h, allowed to cool to 50° C. and poured onto ice water. The yellow solid formed was filtered on a Buckner funnel, washed with H2O and dried under vacuum, affording the title compound (1.20 g, 4.51 mmol) as a light brown solid that was used in the next step without any further purification.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. additionpoured onto ice water
  3. customThe yellow solid formed
  4. filtrationwas filtered on a Buckner funnel
  5. washwashed with H2O
  6. customdried under vacuum

Sources & evidence

ORD record
ord-524fa29ea3114074b2f84a38a7b49a08
Source dataset
uspto-grants-2014_05
Patent number
US08729098B2

Reaction notes

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