Water → 5-(Acetyloxy)-3,4-dihydro-1(2H)-isoquinolinone

HRID 1645899Notes

Reaction equation

HRID 1645899 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][C:7]2=[O:12].C([O-])([O-])=O.[K+].[K+].[C:19](OC(=O)C)(=[O:21])[CH3:20].O>CN(C=O)C>[C:19]([O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][C:7]2=[O:12])(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic Anhydride2×HCID 11430Potassium CarbonateHCID 132366635-Hydroxy-1,2,3,4-tetrahydroisoquinolin-1-one

Product 1

HCID 183695045-(Acetyloxy)-3,4-dihydro-1(2H)-isoquinolinoneYield 47.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.0 g (12.3 mmol) of 3,4-dihydro-5-hydroxy-1(2H)-isoquinolinone, 2.0 g (52 mmol) of K2CO3 and 0.75 g of acetic anhydride in 20 ml of DMF was stirred at room temperature for 2.5 days. The mixture was then warmed to 70°-80° and an additional 1.5 g of acetic anhydride was added and stirring was continued for five hours. The reaction was poured into 250 ml of water and the resulting solid was collected, washed with water, and air dried. It was recrystallized from EtOH and then chromatographed (SiO2, 9:1 methylene chloride/MeOH) to give 0.72 g (29%) of product; mp 189°-193°.

Workup

  1. temperatureThe mixture was then warmed to 70°-80°
  2. stirringstirring
  3. waitwas continued for five hours
  4. customthe resulting solid was collected
  5. washwashed with water, and air
  6. customdried
  7. customIt was recrystallized from EtOH
  8. customchromatographed (SiO2, 9:1 methylene chloride/MeOH)

Sources & evidence

ORD record
ord-848e92578a69489ebbd47f2a70aebe0b
Source dataset
uspto-grants-1993_01
Patent number
US05177075

Reaction notes

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