Hydrogen Bromide → 4-(4-((dimethylamino)methyl)phenyl)-5-hydroxyisoquinolin-1(2H)-one

HRID 31107Notes

Reaction equation

HRID 31107 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[OH:21])[C:14]([O:22]C)=[N:13][CH:12]=2)=[CH:7][CH:6]=1)[CH3:3].Br.O>C(O)(=O)C>[CH3:3][N:2]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[OH:21])[C:14](=[O:22])[NH:13][CH:12]=2)=[CH:9][CH:10]=1)[CH3:1]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962Water2×HCID 692021304-{4-[(Dimethylamino)methyl]phenyl}-1-methoxyisoquinolin-5-ol

Product 1

HCID 98390734-(4-((dimethylamino)methyl)phenyl)-5-hydroxyisoquinolin-1(2H)-oneYield 68%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Process 2: To a solution of 4-[4-(dimethylaminomethyl)phenyl]-5-hydroxy-1-methoxyisoquinoline (102 mg, 331 μmol) in acetic acid (15 mL) were added 47% hydrobromic acid (1.5 mL) and water (1.5 mL), and the mixture was refluxed for 1 hour. Water was added to the residue obtained by concentrating the reaction mixture under reduced pressure, which was made basic with saturated aqueous solution of sodium hydrogen carbonate. The precipitated crystals were collected by filtration, washed with water, and then air-dried, thereby affording 66.2 mg of the title compound as brown powder. Yield 68%.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. customobtained
  3. concentrationby concentrating the reaction mixture under reduced pressure, which
  4. filtrationThe precipitated crystals were collected by filtration
  5. washwashed with water
  6. customair-dried

Sources & evidence

ORD record
ord-dd86daa1f77f40a79f15fd675ff7e23a
Source dataset
uspto-grants-2008_09
Patent number
US07425563B2

Reaction notes

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