Methanol → 6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

HRID 750118Notes

Reaction equation

HRID 750118 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH: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.S(=O)(=O)(O)O.[CH3:27]O>>[CH3:27][O:14][C:13]([C:6]1[NH:7][C:8](=[O:12])[C:9]2[C:4]([C:5]=1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=2)=[O:15]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 230608236-Bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid

Product 1

HCID 691573826-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

Procedure

To the obtained 6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid were added methanol (400 ml) solution and sulfuric acid (40 ml) and the mixture was refluxed for 20 hrs. The reaction mixture was concentrated, and the residue was neutralized with aqueous potassium carbonate solution and extracted with chloroform. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated to give the title compound (6.51 g) as colorless crystals.

Workup

  1. temperaturethe mixture was refluxed for 20 hrs
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6fa710412b40484b9fba0c92c3e23da3
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

Loading…