Methanol → 7-Chloro-6-((4-oxocyclohexyl)oxy)isoquinolin-1(2H)-one

HRID 2370289Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8](CC3C=CC(OC)=CC=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.CO>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][NH:8][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

Conditions

Temperature: 150 °C

Procedure

800 mg (1.94 mmol) of 7-chloro-6-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-2-(4-methoxy-benzyl)-2H-isoquinolin-1-one (65) were dissolved in 3 mL of TFA and heated in a microwave oven at 150° C. for 3 h. Methanol was added and the reaction mixture was evaporated. The crude product was purified by silica gel chromatography to yield 230 mg of 7-chloro-6-(4-oxo-cyclohexyloxy)-2H-isoquinolin-1-one (67). Rt=1.02 min (Method C). Detected mass: 292.1 (M+H+).

Workup

customthe reaction mixture was evaporated
customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record: ord-b793b6966c5a4280b5d8cc268c5ff17f
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710077B2

Reaction notes

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