1-t-Butoxy-3-chloroisoquinoline → 3-CHLORO-2H-ISOQUINOLIN-1-ONE

HRID 1826249Notes

Reaction equation

HRID 1826249 reaction equation
C([O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]([Cl:16])[N:7]=1)(C)(C)C>C(O)=O.O>[Cl:16][C:8]1[NH:7][C:6](=[O:5])[C:15]2[C:10]([CH:9]=1)=[CH:11][CH:12]=[CH:13][CH:14]=2

Participants

4

Reactant 1

HCID 221415801-t-Butoxy-3-chloroisoquinoline

Product 1

HCID 7351463-CHLORO-2H-ISOQUINOLIN-1-ONEYield 78.8%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

0.5 g (2.12 mmol) of 1-t-butoxy-3-chloroisoquinoline from example 16.3 was dissolved in 5.0 ml of formic acid and stirred at room temperature for 20 h. The solution was then diluted with 10 ml of H2O, and the precipitated solid was filtered off through a glass frit, washed with 10 ml of H2O/formic acid (2:1) and dried under high vacuum. 0.30 g (1.67 mmol, 78.8%) of 3-chloroisoquinolin-1(2H)-one was obtained. The combined aqueous phases were concentrated to dryness under reduced pressure and the resulting solid was purified by column chromatography (5:1 dichloromethane/ethyl acetate), whereupon a further 0.040 g (0.22 mmol, 10.4%) of 3-chloroisoquinolin-1(2H)-one was obtained.

Workup

  1. filtrationthe precipitated solid was filtered off through a glass frit
  2. washwashed with 10 ml of H2O/formic acid (2:1)
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-e93b6bad444647af88123f04ff738a57
Source dataset
uspto-grants-2006_05
Patent number
US07049473B2

Reaction notes

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