Ammonium Acetate → 7-Bromo-6-fluoro-1,2-dihydroisoquinolin-1-one

HRID 1930219Notes

Reaction equation

HRID 1930219 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2Cl)=[CH:4][C:3]=1[F:13].C([O-])(=[O:16])C.[NH4+]>C(O)(=O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][NH:8][C:9]2=[O:16])=[CH:4][C:3]=1[F:13]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 598182627-Bromo-1-chloro-6-fluoroisoquinoline

Product 1

HCID 598182537-Bromo-6-fluoro-1,2-dihydroisoquinolin-1-oneYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

12.9 g (49.5 mmol) 7-bromo-1-chloro-6-fluoro-isoquinoline (311) were dissolved in 250 mL of acetic acid. After adding 38.7 g (0.5 mol) ammonium acetate, the solution was stirred at 100° C. After 3 h, the solvent was removed i. vac. and the residue was poured on water. The precipitate was filtered and dried to yield 9.91 g (83%) of the title compound. Rt=1.15 min (Method C). Detected mass: 242.2/244.1 (M+H+).

Workup

  1. customthe solvent was removed i
  2. additionand the residue was poured on water
  3. filtrationThe precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-e59befaa23aa446cb0844059c8df8d73
Source dataset
uspto-grants-2012_05
Patent number
US08188117B2

Reaction notes

Loading…