Ammonium Acetate → 6-Bromoisoquinolin-1(2H)-one

HRID 404719Notes

Reaction equation

HRID 404719 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](Cl)=[N:7][CH:6]=[CH:5]2.C([O-])(=[O:15])C.[NH4+]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:15])[NH:7][CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 222502446-Bromo-1-chloro-isoquinoline

Product 1

HCID 158851826-Bromoisoquinolin-1(2H)-oneYield 72.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 42.8 g (173.5 mmol) of 6-Bromo-1-chloro-isoquinoline (5) in 700 ml of acetic acid were added 133.6 g (1.74 mol) ammonium acetate. After stirring at 100° C. for 3 h, the solution was cooled to room temperature and the solvent was removed i. vac. to a small volume. The residue was poured on water and the suspension was stirred for some minutes. The precipitate was isolated by filtration and dried, to yield 28.2 g of the title compound. Rt=1.30 min (Method B). Detected mass: 224.0 (M+H+).

Workup

  1. temperaturethe solution was cooled to room temperature
  2. customthe solvent was removed i
  3. additionThe residue was poured on water
  4. stirringthe suspension was stirred for some minutes
  5. customThe precipitate was isolated by filtration
  6. customdried

Sources & evidence

ORD record
ord-05789c1f973f434ebf59364a14d07d4d
Source dataset
uspto-grants-2014_06
Patent number
US08748614B2

Reaction notes

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