Benzylamine → 2-benzyl-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid

HRID 750129Notes

Reaction equation

HRID 750129 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10](=[CH:11][CH:12]=1)[C:8](=[O:9])O[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.[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CO>[CH2:22]([N:29]1[C:6]([C:13]([OH:15])=[O:14])=[C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:4]2[C:10](=[CH:11][CH:12]=[C:2]([Br:1])[CH:3]=2)[C:8]1=[O:9])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 230607776-Bromo-4-phenyl-3-isocoumarincarboxylic acid

Product 1

HCID 230606482-benzyl-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic AcidYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-bromo-4-phenyl-3-isocoumarincarboxylic acid (1.00 g) in methanol (20 ml) was added benzylamine (3.16 ml) and the mixture was stirred at room temperature for 2 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 successively with 1N hydrochloric acid and saturated brine and magnesium sulfate was added to dry the mixture. The solvent was evaporated under reduced pressure, and 4N hydrogen chloride-ethyl acetate solution (17 ml) was added to the obtained residue, and the mixture was stirred at room temperature for 18 hrs. The solvent was evaporated under reduced pressure, and addition of water allowed crystal precipitation. The obtained crystals were collected by filtration, washed successively with water and ether and dried under reduced pressure at 50° C. to give the title compound (921 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 successively with 1N hydrochloric acid and saturated brine and magnesium sulfate
  5. additionwas added
  6. customto dry the mixture
  7. customThe solvent was evaporated under reduced pressure, and 4N hydrogen chloride-ethyl acetate solution (17 ml)
  8. additionwas added to the obtained residue
  9. stirringthe mixture was stirred at room temperature for 18 hrs
  10. customThe solvent was evaporated under reduced pressure, and addition of water allowed crystal precipitation
  11. filtrationThe obtained crystals were collected by filtration
  12. washwashed successively with water and ether
  13. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-ff60354c4f1d47f69d71a141a1152a15
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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