Ammonia methanol → 6-Bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid

HRID 750117Notes

Reaction equation

HRID 750117 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10](=[CH:11][CH:12]=1)[C:8](=O)[O:7][C:6]([C:13]([OH:15])=[O:14])=[C:5]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[NH3:22].CO>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:10](=[CH:11][CH:12]=1)[C:8](=[O:7])[NH:22][C:6]([C:13]([OH:15])=[O:14])=[C:5]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 21705897Ammonia methanolHCID 230607776-Bromo-4-phenyl-3-isocoumarincarboxylic acid

Product 1

HCID 230608236-Bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-bromo-4-phenylisocoumarin-3-carboxylic acid (15 g) in methanol (100 ml) was added 12% ammonia-methanol solution (60 ml) and the mixture was stirred at room temperature for 24 hrs. The reaction mixture was concentrated, and 1N hydrochloric acid was added to the obtained residue. The mixture was extracted with ethyl acetate. The organic layer was dried and concentrated and 4N hydrochloric acid ethyl acetate solution (30 ml) was added to the obtained oily substance. The mixture was stirred at room temperature for 2 hrs. and the reaction mixture was concentrated. The obtained crystal was washed with water and dried under reduced pressure to give 6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid as colorless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition1N hydrochloric acid was added to the obtained residue
  3. extractionThe mixture was extracted with ethyl acetate
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. addition4N hydrochloric acid ethyl acetate solution (30 ml) was added to the obtained oily substance
  7. stirringThe mixture was stirred at room temperature for 2 hrs
  8. concentrationand the reaction mixture was concentrated
  9. washThe obtained crystal was washed with water
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-5c0e50401dff49b9b17fb8e84ee17397
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

Loading…