Hydrogen Bromide → 5-Bromoisoquinoline

HRID 2307785Notes

Reaction equation

HRID 2307785 reaction equation
N[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.N([O-])=O.[Na+].[OH-].[Na+].[BrH:18]>O>[Br:18][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2

Participants

6

Reactant 4

HCID 260Hydrogen Bromide2×HCID 14798Sodium HydroxideHCID 707665-AminoisoquinolineHCID 23668193Sodium Nitrite

Product 1

HCID 7364875-BromoisoquinolineYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of 5-aminoisoquinoline (2.0 g, 13.8 mmol) and 48% HBr (6 mL) in 20 mL water cooled to 0° C. was added a solution of sodium nitrite (0.95 g, 13.8 mmol) in 6 mL water. The solution was stirred at 0° C. for 20 minutes. The solution, while kept at 0° C., was added to a solution of CuBr (2.11 g, 15.9 mmol) in 48% HBr (4.77 mL) and water (10 mL). The reaction was stirred at room temperature for an additional 1 hr. The reaction was neutralized with NaOH (50%) and extracted with ethyl acetate (3×). The combined organic layer was concentrated in vacuo and chromatographed using 1:1 hexanes/ethyl acetate to yield 1.4 g product (50%).

Workup

  1. customwhile kept at 0° C.
  2. stirringThe reaction was stirred at room temperature for an additional 1 hr
  3. extractionextracted with ethyl acetate (3×)
  4. concentrationThe combined organic layer was concentrated in vacuo
  5. customchromatographed

Sources & evidence

ORD record
ord-5d8054a006bc4a30b487044552e9a93a
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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