Triethylamine → 6-Bromo-2-(4-methanesulfonylbenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid

HRID 750282Notes

Reaction equation

HRID 750282 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.Cl.[CH3:23][S:24]([C:27]1[CH:34]=[CH:33][C:30]([CH2:31][NH2:32])=[CH:29][CH:28]=1)(=[O:26])=[O:25].C(N(CC)CC)C>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:10](=[CH:11][CH:12]=1)[C:8](=[O:9])[N:32]([CH2:31][C:30]1[CH:29]=[CH:28][C:27]([S:24]([CH3:23])(=[O:26])=[O:25])=[CH:34][CH:33]=1)[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

5

Reactant 3

HCID 8471TriethylamineHCID 27292694-Methylsulfonylbenzylamine hydrochlorideHCID 230607776-Bromo-4-phenyl-3-isocoumarincarboxylic acid

Product 1

HCID 230609586-Bromo-2-(4-methanesulfonylbenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acidYield 77.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 6-bromo-4-phenyl-3-isocoumarincarboxylic acid (1.25 g) in methanol (20 ml) were added 4-methanesulfonylbenzylamine hydrochloride (1.6 g) and triethylamine (2.5 ml), and the mixture was stirred at 50° C. for 18 hrs. The solvent was evaporated under reduced pressure, and the residue was diluted with ethyl acetate, washed with 1N hydrochloric acid, and dried. The solvent was evaporated under reduced pressure. 4N Hydrochloric acid ethyl acetate solution (10 ml) was added to the residue, and the mixture was stirred at room temperature for 18 hrs. The precipitate was collected by filtration, washed with diethyl ether and dried to give the title compound (1.43 g).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with 1N hydrochloric acid
  4. customdried
  5. customThe solvent was evaporated under reduced pressure
  6. addition4N Hydrochloric acid ethyl acetate solution (10 ml) was added to the residue
  7. stirringthe mixture was stirred at room temperature for 18 hrs
  8. filtrationThe precipitate was collected by filtration
  9. washwashed with diethyl ether
  10. customdried

Sources & evidence

ORD record
ord-87e45a618dac421f8184e542dc8a90b6
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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