Ethyl Acetate → 5-Bromo-6-isoquinolinol

HRID 1022855Notes

Reaction equation

HRID 1022855 reaction equation
[Br:1]Br.[OH:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[N:9][CH:8]=[CH:7]2.C(OCC)(=O)C>C(Cl)(Cl)Cl>[Br:1][C:5]1[C:4]([OH:3])=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][N:9]=[CH:10]2

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24408BromineHCID 135483582Isoquinolin-6-ol

Product 1

HCID 1360928955-Bromo-6-isoquinolinolYield 88.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

7.9 mL (19.18 g, 120 mmol) of bromine were added dropwise to a suspension of 17.42 g (120 mmol) of compound 7 in 250 mL of chloroform at room temperature. After stirring for 2 h ethyl acetate was added. The precipitate was filtered, washed with ethyl acetate and dried. Aqueous NaHCO3 solution was added carefully. The precipitate was filtered and washed with NaHCO3 solution until the filtrate had a pH of 8. Drying gave 23.78 g (88%) of compound 9 as an off-white solid.

Workup

  1. additionwas added
  2. filtrationThe precipitate was filtered
  3. washwashed with ethyl acetate
  4. customdried
  5. additionAqueous NaHCO3 solution was added carefully
  6. filtrationThe precipitate was filtered
  7. washwashed with NaHCO3 solution until the filtrate
  8. customDrying

Sources & evidence

ORD record
ord-35a16e94a8964fa2ac77a9a84dc16510
Source dataset
uspto-grants-2014_05
Patent number
US08722671B2

Reaction notes

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