Ammonia → Methyl 2-(6-bromo-1-oxo-1,2-dihydroisoquinolin-3-yl)acetate

HRID 927269Notes

Reaction equation

HRID 927269 reaction equation
[NH3:1].CO.[Br:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=O)[O:10][C:9]([CH2:16][C:17]([O:19][CH2:20]C)=[O:18])=[CH:8]2>>[Br:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:10])[NH:1][C:9]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:8]2

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 90095309HCID 90095309, compound

Product 1

HCID 118558141Methyl 2-(6-bromo-1-oxo-1,2-dihydroisoquinolin-3-yl)acetate

Procedure

A solution of 7 N ammonia in MeOH (3.14 mL, 21.95 mmol, 10.0 equiv.) and ethyl 2-(6-bromo-1-oxo-1H-isochromen-3-yl)acetate (683 mg, 2.195 mmol) was stirred at room temperature for 1 h. Upon completion of the reaction, the excess solvent was concentrated, diluted with 1 N HCl (5 mL), and extracted with EtOAc (2×5 mL). The organic layer was dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by column chromatography on silica gel eluting with 0-40% EtOAc/hexanes to give 250 mg of methyl 2-(6-bromo-1-oxo-1,2-dihydroisoquinolin-3-yl)acetate as a white solid.

Workup

  1. customUpon completion of the reaction
  2. concentrationthe excess solvent was concentrated
  3. additiondiluted with 1 N HCl (5 mL)
  4. extractionextracted with EtOAc (2×5 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue was purified by column chromatography on silica gel eluting with 0-40% EtOAc/hexanes

Sources & evidence

ORD record
ord-64ded6c30b9c48d88259194e81229e18
Source dataset
uspto-grants-2016_03
Patent number
US09290454B2

Reaction notes

Loading…