1-[1-(4-Chlorophenyl)cyclobutyl]-7-methoxy-3,4-dihydroisoquinoline → 1-[1-(4-Chlorophenyl)cyclobutyl]-3,4-dihydroisoquinolin-7-ol

HRID 242086

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:22]C)[CH:20]=4)[CH2:15][CH2:14][N:13]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1>Br>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([OH:22])[CH:20]=4)[CH2:15][CH2:14][N:13]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

The crude 1-[1-(4-chlorophenyl)cyclobutyl]-7-methoxy-3,4-dihydroisoquinoline (10.25 g, 30.8 mmol) was treated with 47% aqueous hydrobromic acid (109 mL) and stirred at 120° C. for 4 h. The reaction mixture was cooled to room temperature. The aqueous layer was decanted. The crude product was treated with dichloromethan, methanol and water and the pH was adjusted to 10 with aqueous 1N sodium hydroxide solution. The product precipitated and the solid was collected by filtration. The product was washed with water and dried in vacuo at 30° C. Yield: 3.56 g (30.3, 12.38 mmol).

Workup

temperatureThe reaction mixture was cooled to room temperature
customThe aqueous layer was decanted
additionThe crude product was treated with dichloromethan, methanol and water
customThe product precipitated
filtrationthe solid was collected by filtration
washThe product was washed with water
customdried in vacuo at 30° C

Sources & evidence

ORD record: ord-bf2362efddad4e5b9dec6b8942f56e9f
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653100B2

Linked notes

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