Hydrogen Bromide → 5-(Bromomethyl)isoquinoline hydrobromide

HRID 1831921Notes

Reaction equation

HRID 1831921 reaction equation
[CH:1]1[C:10]2[C:5](=[C:6]([CH2:11]O)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[BrH:13]>CC(O)=O>[BrH:13].[Br:13][CH2:11][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[CH:3][N:2]=[CH:1]2

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 12832770Isoquinolin-5-ylmethanol

Product 1

HCID 497617055-(Bromomethyl)isoquinoline hydrobromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of isoquinolin-5-ylmethanol (0.63 g, 3.9 mmol) in AcOH (3.3 mL) was added HBr (6.6 mL, a 30% w/w solution in AcOH, 24 mmol), and the reaction mixture was stirred at 75° C. for 45 min. The reaction mixture was cooled to room temperature, and the precipitate was collected to provide the 5-bromomethylisoquinoline hydrobromide acid salt as a brown solid (1.1 g, 87%): 1H NMR (300 MHz, CDCl3) δ 9.22 (s, 1H), 8.58 (d, J=6 Hz, 1H), 7.95-7.89 (m, 2H), 7.76 (d, J=9 Hz, 1H), 7.59 (dd, J=9, 6 Hz, 1H), 5.16 (s, 2H).

Workup

  1. customthe precipitate was collected

Sources & evidence

ORD record
ord-06f5928a5767487ea1e07ce979be7e84
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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