Boron tribromide → 2-Dimethylaminomethyl-9-hydroxythieno[2,3-c]isoquinolin-5(4H)-one hydrobromide

HRID 472672Notes

Reaction equation

B(Br)(Br)[Br:2].Cl.[CH3:6][N:7]([CH2:9][C:10]1[S:25][C:13]2[NH:14][C:15](=[O:24])[C:16]3[CH:17]=[CH:18][CH:19]=[C:20]([O:22]C)[C:21]=3[C:12]=2[CH:11]=1)[CH3:8]>ClCCl>[BrH:2].[CH3:8][N:7]([CH2:9][C:10]1[S:25][C:13]2[NH:14][C:15](=[O:24])[C:16]3[CH:17]=[CH:18][CH:19]=[C:20]([OH:22])[C:21]=3[C:12]=2[CH:11]=1)[CH3:6]

Participants

Conditions

Temperature: 23 °C

Procedure

Boron tribromide, 1 M CH2Cl2 solution, (0.1 ml, 0.41 mmol) was added to a solution of 2-dimethylaminomethyl-9-methoxythieno[2,3-c]isoquinolin-5(4H)-one hydrochloride (0.03 g, 0.09 mmol) in dichloromethane (2 ml) and the reaction mixture was refluxed for 24 hours. The mixture was cooled to 23° C., poured on to ice and the resulting mixture was evaporated under reduced pressure. The mixture was purified by crystallization with 96% ethanol to obtain the title compound (54% yield) as pure solid.

Workup

temperaturethe reaction mixture was refluxed for 24 hours
additionpoured on to ice
customthe resulting mixture was evaporated under reduced pressure
customThe mixture was purified by crystallization with 96% ethanol

Sources & evidence

ORD record: ord-732c638f829c401ab1bfae804137cdcc
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633215B2

Reaction notes

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