HCID 86685982, compound → HCID 86685981, compound

HRID 2277686Notes

Reaction equation

HRID 2277686 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([C:13]1[CH:14]=[N:15][CH:16]=[C:17]([O:19]C)[CH:18]=1)[CH2:6][CH2:5]2>Br>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([C:13]1[CH:14]=[N:15][CH:16]=[C:17]([OH:19])[CH:18]=1)[CH2:6][CH2:5]2

Participants

3

Reactant 1

HCID 86685982HCID 86685982, compound

Product 1

HCID 86685981HCID 86685981, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

6-Chloro-2-(5-methoxy-pyridin-3-yl)-3,4-dihydro-2H-isoquinolin-1-one (1.44 g, 5 mmol, example 10) was dissolved in aq. HBr (48%, 20 mL). The reaction mixture was heated to reflux temperature and stirred overnight. After cooling to room temperature, it was carefully neutralized with satd. aq. NaHCO3 solution and extracted with EtOAc (2×25 mL). The organic layer was dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product (1.02 g, 74%) as brown oil. MS: 275.1 (M+H+).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux temperature
  3. extractionaq. NaHCO3 solution and extracted with EtOAc (2×25 mL)
  4. customThe organic layer was dried over anhy
  5. filtrationNa2SO4, filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c1c1fe5d28ed4706b19da39fc1522940
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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