Water → HCID 20139720, compound

HRID 4483Notes

Reaction equation

HRID 4483 reaction equation
[OH-].[Na+].[CH2:3]([C:6]1[CH:7]=[C:8]2[C:14](=[O:15])[N:13]([C:16]([CH:21]([CH3:23])[CH3:22])([CH3:20])[C:17]([NH2:19])=[O:18])[C:12](=O)[C:9]2=[N:10][CH:11]=1)[CH2:4][CH3:5].O>C1(C)C=CC=CC=1>[CH:21]([C:16]1([CH3:20])[N:13]2[C:14](=[O:15])[C:8]3[C:9](=[N:10][CH:11]=[C:6]([CH2:3][CH2:4][CH3:5])[CH:7]=3)[C:12]2=[N:19][C:17]1=[O:18])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 20139714alpha-[3-n-propyl-6H-pyrrolo[3,4-b]pyridine-5,7-dione-6-yl]-alpha-isopropyl-alpha-methyl-acetamide

Product 1

HCID 20139720HCID 20139720, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

With the simultaneous addition of 0.5 g of powdered sodium hydroxide, a solution of α-[3-n-propyl-6H-pyrrolo[3,4-b]pyridine-5,7-dione-6-yl]-α-isopropyl-α-methyl-acetamide (m.p.: 82° C.) in 100 ml of toluene is heated under reflux for 2 hours in a water separator. After the reaction solution has cooled, it is filtered through silica gel and the filtrate is washed with ethyl acetate and then concentrated by evaporation. The residue is recrystallised from ethyl acetate/petroleum ether, affording 13.1 g of the title compound which melts at 116° C.

Workup

  1. temperatureAfter the reaction solution has cooled
  2. filtrationit is filtered through silica gel
  3. washthe filtrate is washed with ethyl acetate
  4. concentrationconcentrated by evaporation
  5. customThe residue is recrystallised from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-a5f8cf3706fb4e88af4fdf400f66f3e5
Source dataset
uspto-grants-1988_02
Patent number
US04726838

Reaction notes

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