Hydrochloric Acid → HCID 19363444, compound

HRID 850498Notes

Reaction equation

HRID 850498 reaction equation
O[CH2:2][CH2:3][C:4]1[C:28]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[C:27]([O:35][CH3:36])[CH:26]=[CH:25][C:5]=1[C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1)=[O:7].C(N(CC)CC)C.Cl.C(OCC)(=O)C>CS(C)=O>[CH2:18]([O:17][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][CH2:9][N:8]2[CH:2]=[CH:3][C:4]3[C:5](=[CH:25][CH:26]=[C:27]([O:35][CH3:36])[C:28]=3[O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:6]2=[O:7])=[CH:16][CH:15]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 19363348HCID 19363348, compound

Product 1

HCID 19363444HCID 19363444, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-(2-Hydroxyethyl)-4-methoxy-3-pentyloxy-N-[2-(4-benzyloxyphenyl)-ethyl]benzamide (1.33 g, 2.7 mmol, 1.0 eq) was dissolved in DMSO (26 ml), and triethylamine (3.49 ml, 24.3 mmol, 9 eq) and sulfur trioxide-pyridine complex (1.29 g, 8.1 mmol, 3 eq) were successively added under ice-cooling. The mixture was stirred at room temperature for 2 hours. 3N Hydrochloric acid (35 ml) was added to this reaction mixture. The mixture was stirred at room temperature for 30 minutes and e xacted twice with ethyl acetate (40 ml). The organic layers were combined, washed with a saturated aqueous sodium carbonate solution (40 ml) and saturated brine (100 ml), and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (ethyl acetate/hexane=2/1) to give 2-[2-(4-benzyloxyphenyl)ethyl]-6-methoxy-5-pentyloxy-2H-isoquinolin-1-one (1.275 g, 100%) as colorless crystals.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 30 minutes
  3. washwashed with a saturated aqueous sodium carbonate solution (40 ml) and saturated brine (100 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe drying agent was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by column chromatography on silica gel (ethyl acetate/hexane=2/1)

Sources & evidence

ORD record
ord-4a9103ce39de4f6799524e0ed673c975
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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