Hydrochloric Acid → HCID 68511825, compound

HRID 2196395Notes

Reaction equation

HRID 2196395 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([CH2:14][CH2:15][CH2:16][N:17]1C(=O)C3C(=CC=CC=3)C1=O)[C:7]([CH3:28])=[C:6]2[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.NN.[ClH:37]>CO.[Cl-].[Na+].O>[Cl-:37].[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([CH2:14][CH2:15][CH2:16][NH3+:17])[C:7]([CH3:28])=[C:6]2[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 68510088HCID 68510088, compound

Product 1

HCID 68511825HCID 68511825, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-[3-(6-methoxy-3-methyl-1-oxo-4-phenylisoquinolin-2(1H)-yl)propyl]-1H-isoindole-1,3(2H)-dione (0.46 g) was dissolved in 20 mL methanol, and hydrazine (0.100 mL) was added. The reaction was stirred overnight at room temp, then diluted with brine and extracted with EtOAc (3×). The combined organic solutions were dried (Na2SO4) and concentrated. Flash chromatography (5% MeOH in CH2Cl2) gave a solid, which was treated with excess HCl and recrystallized from isopropanol/diethyl ether to give the titled compound.

Workup

  1. extractionextracted with EtOAc (3×)
  2. dry with materialThe combined organic solutions were dried (Na2SO4)
  3. concentrationconcentrated
  4. customFlash chromatography (5% MeOH in CH2Cl2) gave a solid, which
  5. customrecrystallized from isopropanol/diethyl ether

Sources & evidence

ORD record
ord-eebefdcd63094afda2309e7c707b2160
Source dataset
uspto-grants-2012_12
Patent number
US08338449B2

Reaction notes

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