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

HRID 1042248Notes

Reaction equation

HRID 1042248 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>[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

4

Reactant 2

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

Product 1

HCID 589422595-hydroxy-6-methylisoquinolin-1(2H)-oneYield 69.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

5-Amino-6-methylisoquinolin-1(2H)-one (2.00 g, 11.48 mmol) was dissolved in sulfuric acid (24.3 mL, 287 mmol) (75%, 35 mL). The solution was cooled to 0° C. then a solution of sodium nitrite (12.1 mmol) in sulfuric acid (5 mL) was added dropwise over 15 min. The resulting solution was stirred at 0° C. for 45 min and then the reaction mixture was heated to 70° C. and stirred for 16 h. The reaction mixture was cooled in an ice bath for 15 min, then 100 g of ice was added. The mixture was filtered. The filter cake was washed with water for 4 times until the filtrate became neutral by pH paper. The filter cake was air dried to give 5-hydroxy-6-methylisoquinolin-1(2H)-one as a dark gray solid (1.39 g, 69% yield). MS (ESI, pos. ion) m/z: 176 [M+H]+

Workup

  1. temperaturethe reaction mixture was heated to 70° C.
  2. stirringstirred for 16 h
  3. temperatureThe reaction mixture was cooled in an ice bath for 15 min
  4. filtrationThe mixture was filtered
  5. washThe filter cake was washed with water for 4 times until the filtrate
  6. customdried

Sources & evidence

ORD record
ord-92ec3968aa2148b3bd131ebdc4764a0c
Source dataset
uspto-grants-2013_10
Patent number
US08557830B2

Reaction notes

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