Hydrochloric Acid → HCID 19363356, compound

HRID 850502Notes

Reaction equation

HRID 850502 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[C:19](OC)=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:11]2=[O:28])=[CH:4][CH:3]=1.N1C(C)=CC=C[C:30]=1[CH3:36].[C:37](OC(=O)C)(=[O:39])C.Cl.[OH2:45]>ClCCl>[C:30]([O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:39][CH3:37])[C:16]=3[O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:11]2=[O:28])=[CH:4][CH:3]=1)(=[O:45])[CH3:36]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 7918Acetic AnhydrideHCID 79372,6-LutidineHCID 19363446HCID 19363446, compound

Product 1

HCID 19363356HCID 19363356, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[2-(4-Hydroxyphenyl)ethyl]-methoxy-5-pentyloxy-2H-isoquinolin-1-one (681.8 mg, 1.79 mmol, 1.0 eq) was dissolved in dichloromethane (7 ml), and 2,6-lutidine (575 mg, 5.36 mmol, 3 eq) and acetic anhydride (1.13 g, 5.36 mmol, 3 eq) were successively added under ice-cooling. The mixture was stirred at room temperature for 12 hours and refluxed under heating for 3 hours. The reaction mixture was cooled to room temperature, and water (10 ml) and a 10% aqueous hydrochloric acid solution (10 ml) were successively added. The miture was extracted twice with dichloromethane (30 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/ hexane=1/1) to give 4-[2-(6-methoxy-1-oxo-5-pentyloxy-1H-isoquinolin-2-yl)ethyl]phenyl acetate (734 mg, 97.0%) as colorless crystals.

Workup

  1. temperaturecooling
  2. temperaturerefluxed
  3. temperatureunder heating for 3 hours
  4. temperatureThe reaction mixture was cooled to room temperature
  5. extractionThe miture was extracted twice with dichloromethane (30 ml)
  6. washwashed with saturated brine (40 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationThe drying agent was filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe obtained residue was purified by column chromatography on silica gel (ethyl acetate/ hexane=1/1)

Sources & evidence

ORD record
ord-01c0c284daae4b34853d1579e57b84f8
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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