Hydrochloric Acid → HCID 19363523, compound

HRID 850500Notes

Reaction equation

HRID 850500 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:20]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[C:19](OC)[CH:18]=[CH:17][C:5]=1[C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)=[O:7].[CH2:29](N(CC)CC)C.Cl.[OH-].[Na+]>CS(C)=O>[N:14]1[CH:13]=[CH:12][C:11]([CH2:10][CH2:9][N:8]2[C:2]([O:1][CH3:29])=[CH:3][C:4]3[C:5](=[CH:17][CH:18]=[CH:19][C:20]=3[O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:6]2=[O:7])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 19363399HCID 19363399, compound

Product 1

HCID 19363523HCID 19363523, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-(2-Hydroxyethyl)-4-methoxy-3-pentyloxy-N-(2-pyridin-4-ylethyl)-benzamide (90 mg, 233 mmol, 1.0 eq) was dissolved in DMSO (2 ml), and triethylamine (0.3 ml, 2.10 mmol, 9 eq) and sulfur trioxide-pyridine complex (111.2 mg, 0.70 mmol, 3 eq) were successively added under ice-cooling. The mixture was stirred at room temperature for 4 hours. 3N Hydrochloric acid (15 ml) was added to this reaction mixture, and the mixture was stirred at room temperature for 1 hour. Sodium hydroxide was added to make the same alkaline. The solution was extracted twice with ethyl acetate (20 ml). The organic layers were combined, washed with saturated brine (40 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) and recrystallized from ethyl acetate to give 2-[2-(4-pyridyl)ethyl]-methoxy-5-pentyloxy-2H-isoquinolin-1-one (40.2 mg, 47.1%) as colorless crystals.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. extractionThe solution was extracted twice with ethyl acetate (20 ml)
  4. washwashed with saturated brine (40 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe drying agent was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe obtained residue was purified by column chromatography on silica gel (ethyl acetate)
  9. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-bb8638b5fbb0417e8448b3c0ff53e92c
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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