Ammonium Chloride → HCID 21710454, compound

HRID 650942Notes

Reaction equation

HRID 650942 reaction equation
[Br-].[NH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][N+:7]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:8]2.[CH3:20][Mg]Cl.[Cl-].[NH4+]>C1COCC1>[NH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][N:7]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:8]2[CH3:20]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21710449HCID 21710449, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 21710454HCID 21710454, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To solution of 5-aminoisoquinoline (15 g, 104 mmol) in acetone (400 ml) was added benzyl bromide (18.6 ml, 156 mmol). The mixture was stirred at room temp for 2 h before the precipitate was filtered off affording an orange solid (8.64 g). A second crop (4.02 g) was filtered after a further 2 h. To a solution of this 5-amino-2-benzyl-isoquinolinium bromide (8.46 g, 26.8 mmol) in THF (75 ml) at 0° C. under argon was added dropwise methyl magnesium chloride (17.89 ml, 56.6 mmol). The mixture was allowed to warm up to room temperature and was stirred for 2 h. The mixture was then poured into ammonium chloride solution and extracted with ether. The organic layer was dried over sodium sulfate and concentrated in vacuo to afford the title compound as a light brown solid (5.0 g).

Workup

  1. filtrationA second crop (4.02 g) was filtered after a further 2 h
  2. extractionextracted with ether
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-880f9ca501a34e239832a1ee8aeb08d5
Source dataset
uspto-grants-2001_08
Patent number
US06277861B1

Reaction notes

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