Sodium Bicarbonate → 7-Chloro-2-(4-methoxy-benzyl)-6-(4-oxo-cyclohexyloxy)-2H-isoquinolin-1-one

HRID 2370288Notes

Reaction equation

HRID 2370288 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[C:9]2=[O:12])=[CH:4][C:3]=1[O:22][CH:23]1[CH2:32][CH2:31][C:26]2(OCC[O:27]2)[CH2:25][CH2:24]1.C(=O)(O)[O-].[Na+]>Cl.CC(C)=O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)[C:9]2=[O:12])=[CH:4][C:3]=1[O:22][CH:23]1[CH2:24][CH2:25][C:26](=[O:27])[CH2:31][CH2:32]1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 592260607-Chloro-6-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-2-(4-methoxy-benzyl)-2H-isoquinolin-1-one

Product 1

HCID 592260557-Chloro-2-(4-methoxy-benzyl)-6-(4-oxo-cyclohexyloxy)-2H-isoquinolin-1-oneYield 69.8%

Reagents, catalysts & solvents 1

HCID 19044839Acetone hydrogen chlorideSolvent

Procedure

1.00 g (2.19 mmol) of 7-chloro-6-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-2-(4-methoxy-benzyl)-2H-isoquinolin-1-one (65) were stirred in 9 ml of 6 N HCl/acetone (1:2) at room temperature. After 2 h the reaction mixture was poured on saturated sodium bicarbonate solution and extracted with dichloromethane. The organic layer was dried with magnesium sulfate and evaporated. The crude product was purified by silica gel chromatography to give 630 mg of the title compound. Rt=1.81 min (Method B). Detected mass: 412.2 (M+H+).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. customevaporated
  4. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-188a816c250a400c9bc06cc3a7b222b4
Source dataset
uspto-grants-2014_04
Patent number
US08710077B2

Reaction notes

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