7-Isoquinolinol → 7-Hydroxy-8-nitroisoquinoline

HRID 963647Notes

Reaction equation

HRID 963647 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[CH:9]2)=[CH:4][CH:3]=1.F[B-](F)(F)F.[O:17]=[N+:18]=[O:19]>C1S(=O)(=O)CCC1>[OH:1][C:2]1[C:11]([N+:18]([O-:19])=[O:17])=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[CH:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4597677-IsoquinolinolHCID 11073463Nitronium tetrafluoroborate

Product 1

HCID 122162817-Hydroxy-8-nitroisoquinoline

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Procedure

To a 300 ml round bottom flask is added 14.5 g (0.1 mole) of 7-hydroxyisoquinoline and 100 ml of warmed tetramethylene sulfone. The brown slurry is stirred and to it is added portionwise 18.6 g (0.14 mole) of nitronium tetrafluoroborate with cooling (ice bath). The reaction is stirred for 3 hours. The reaction is then quenched with 100 ml of methanol, evaporated to dryness and triturated twice with ether to precipitate a dark solid (19.0 g, 100%).

Workup

  1. temperaturewith cooling (ice bath)
  2. stirringThe reaction is stirred for 3 hours
  3. customThe reaction is then quenched with 100 ml of methanol
  4. customevaporated to dryness
  5. customtriturated twice with ether
  6. customto precipitate a dark solid (19.0 g, 100%)

Sources & evidence

ORD record
ord-4c5818ef45404f4d9b901124c1ddeef9
Source dataset
uspto-grants-1998_06
Patent number
US05763611

Reaction notes

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