Hydrochloric Acid → 2-(4-Chloro-2-oxo-1,2-dihydropyridin-3-yl)-6-isopropylimidazo[4,5-f]isoindole-5,7(1H,6H)-dione

HRID 69368Notes

Reaction equation

HRID 69368 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8]C)[C:3]=1[C:10]1[NH:26][C:13]2=[CH:14][C:15]3[C:16](=[O:25])[N:17]([CH:22]([CH3:24])[CH3:23])[C:18](=[O:21])[C:19]=3[CH:20]=[C:12]2[N:11]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[C:3]=1[C:10]1[NH:11][C:12]2=[CH:20][C:19]3[C:18](=[O:21])[N:17]([CH:22]([CH3:23])[CH3:24])[C:16](=[O:25])[C:15]=3[CH:14]=[C:13]2[N:26]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 666894972-(4-Chloro-2-methoxypyridin-3-yl)-6-isopropylimidazo[4,5-f]isoindole-5,7(1H,6H)-dione

Product 1

HCID 1363406532-(4-Chloro-2-oxo-1,2-dihydropyridin-3-yl)-6-isopropylimidazo[4,5-f]isoindole-5,7(1H,6H)-dione

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (2-(4-chloro-2-methoxypyridin-3-yl)-6-isopropylimidazo[4,5-f]isoindole-5,7(1H,6H)-dione (220 mg) in 50 mL of dioxane was added 1 mL of conc. (12 N) HCl. The mixture was heated to reflux and maintained for 3 h. The solvent was removed by rotary evaporation and the solid residue was triturated with n-butanol three times to give a white solid which was used directly in the next step.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperaturemaintained for 3 h
  4. customThe solvent was removed by rotary evaporation
  5. customthe solid residue was triturated with n-butanol three times
  6. customto give a white solid which

Sources & evidence

ORD record
ord-b2e9ced3642f438b905f8f734987f452
Source dataset
uspto-grants-2014_09
Patent number
US08822500B2

Reaction notes

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