Hydrogen Bromide → 1,2,3,4-Tetrahydroisoquinolin-8-ol--hydrogen bromide (1/1)

HRID 2377620Notes

Reaction equation

HRID 2377620 reaction equation
Cl.C[O:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[CH2:12][NH:11][CH2:10][CH2:9]2.[BrH:14]>>[BrH:14].[OH:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[CH2:12][NH:11][CH2:10][CH2:9]2

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 450740448-Methoxy-1,2,3,4-tetrahydroisoquinoline--hydrogen chloride (1/1)

Product 1

HCID 136352161,2,3,4-Tetrahydroisoquinolin-8-ol--hydrogen bromide (1/1)Yield 81%

Conditions

Temperature
120 °C

Procedure

A mixture of 8-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride [Tetrahedron Letters, 1991, 32(17), 1965.] (3.0 g 15.0 mmol) and 45 mL of 48% aqueous HBr was heated for 18 h at 120° C. The resulting brown suspension was filtered and dried to provide 8-hydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide (2.8 g, 81% yield). LRMS (ESI) m/z 150.1 [(M+H)+; calcd for C9H1NO: 150.2].

Workup

  1. filtrationThe resulting brown suspension was filtered
  2. customdried

Sources & evidence

ORD record
ord-8d0db0ee40424111ab401819073ddba4
Source dataset
uspto-grants-2008_12
Patent number
US07470664B2

Reaction notes

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