Hydrogen Bromide → 5,8-Dichloro-1,2,3,4-tetrahydroisoquinoline-6,7-diol hydrobromide

Reaction equation

Cl.[Cl:2][C:3]1[C:12]([O:13]C)=[C:11]([O:15]C)[C:10]([Cl:17])=[C:9]2[C:4]=1[CH2:5][CH2:6][NH:7][CH2:8]2.[BrH:18]>>[BrH:18].[Cl:2][C:3]1[C:12]([OH:13])=[C:11]([OH:15])[C:10]([Cl:17])=[C:9]2[C:4]=1[CH2:5][CH2:6][NH:7][CH2:8]2

Participants

Reactant 2

HCID 260Hydrogen Bromide

HCID 68510317HCID 68510317, compound

Product 1

HCID 685081725,8-Dichloro-1,2,3,4-tetrahydroisoquinoline-6,7-diol hydrobromide

Procedure

5,8-Dichloro-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (1.0 g, 3.35 mmol) was suspended in aqueous HBr (48%, 10 mL) and refluxed for 5 hours before evaporation. The remaining residue was evaporated twice from toluene to give 1.05 g (quant) of the title compound as a pale solid.

Workup

temperaturerefluxed for 5 hours before evaporation
customThe remaining residue was evaporated twice from toluene

Sources & evidence

ORD record: ord-00f51531e9e346a685d5c7b55954a003
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318768B2

Reaction notes

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