Sodium Nitrite → 5-hydroxy-6-methylisoquinolin-1(2H)-one

HRID 2092341Notes

Reaction equation

HRID 2092341 reaction equation
N[C:2]1[C:11]([CH3:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][NH:6][C:7]2=[O:13].N([O-])=[O:15].[Na+]>S(=O)(=O)(O)O.O>[OH:15][C:2]1[C:11]([CH3:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][NH:6][C:7]2=[O:13]

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 529879275-amino-6-methylisoquinolin-1(2H)-one

Product 1

HCID 589422595-hydroxy-6-methylisoquinolin-1(2H)-oneYield 85.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

5-Amino-6-methylisoquinolin-1(2H)-one (1.00 g, 5.74 mmol) was dissolved in 75% sulfuric acid (18.2 ml). Mixture cooled to 0° C. and treated with a solution of sodium nitrite (0.416 g, 6.03 mmol) in concentrated sulfuric acid (2.28 ml). After the mixture had been stirred for 1 hour at this temperature, water (36.0 ml) was added and the mixture warmed to 65° C. overnight. The mixture was then diluted with 150 mL water. The resulting precipitate was filtered and washed with an additional portion of water and Et2O. A brown solid was collected: 5-hydroxy-6-methylisoquinolin-1(2H)-one (0.860 g, 85.5% yield). MS (M+H)+ 176.

Workup

  1. additionwas added
  2. temperaturethe mixture warmed to 65° C. overnight
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with an additional portion of water and Et2O
  5. customA brown solid was collected

Sources & evidence

ORD record
ord-9c063265203c43cd85d0a81a9f2779a9
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

Loading…