(3,5-Dimethoxyphenyl)methanamine → 6-bromo-2-(3,5-dimethoxybenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

HRID 750136Notes

Reaction equation

HRID 750136 reaction equation
[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]([C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:13][C:12]([Br:22])=[CH:11][CH:10]=2)=O)=[O:4].[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:30]=[C:31]([O:33][CH3:34])[CH:32]=1)[CH2:28][NH2:29]>CO>[CH3:1][O:2][C:3]([C:5]1[N:29]([CH2:28][C:27]2[CH:30]=[C:31]([O:33][CH3:34])[CH:32]=[C:25]([O:24][CH3:23])[CH:26]=2)[C:7](=[O:6])[C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:13][C:12]([Br:22])=[CH:11][CH:10]=2)=[O:4]

Participants

4

Reactant 2

HCID 420973(3,5-Dimethoxyphenyl)methanamineHCID 66990710Methyl 6-bromo-1-oxo-4-phenyl-1H-isochromene-3-carboxylate

Product 1

HCID 691572316-bromo-2-(3,5-dimethoxybenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl EsterYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-bromo-4-phenyl-3-isocoumarincarboxylic acid methyl ester (539 mg) in methanol (10 ml) was added 3,5-dimethoxybenzylamine (1.25 g), and the mixture was stirred at room temperature for 12 hrs. The solvent was evaporated under reduced pressure and 1N hydrochloric acid was added. The mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried by adding sodium sulfate. The solvent was evaporated under reduced pressure, and 4N hydrogen chloride ethyl acetate solution (5 ml) was added to the obtained residue. The mixture was stirred at room temperature for 10 hrs. The solvent was evaporated under reduced pressure, water was added and the mixture was extracted with ethyl acetate. The extract was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine and dried by adding sodium sulfate. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=19/1→4/1) to give the title compound (555 mg, 73%).

Workup

  1. customThe solvent was evaporated under reduced pressure and 1N hydrochloric acid
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. customdried
  6. additionby adding sodium sulfate
  7. customThe solvent was evaporated under reduced pressure, and 4N hydrogen chloride ethyl acetate solution (5 ml)
  8. additionwas added to the obtained residue
  9. stirringThe mixture was stirred at room temperature for 10 hrs
  10. customThe solvent was evaporated under reduced pressure, water
  11. additionwas added
  12. extractionthe mixture was extracted with ethyl acetate
  13. washThe extract was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  14. customdried
  15. additionby adding sodium sulfate
  16. customThe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=19/1→4/1)

Sources & evidence

ORD record
ord-68d8a70c6c1a463980aba58d5f91a4c7
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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