Methanol → 5,6-Diamino-2-(2-(dimethylamino)ethyl)-4-methylisoindoline-1,3-dione

HRID 920483Notes

Reaction equation

HRID 920483 reaction equation
[NH2:1][C:2]1[C:3]([CH3:21])=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-])=O)[C:7](=[O:14])[N:6]([CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])[C:5]2=[O:20].CO.[H][H]>[Pd].C(O)(=O)C>[NH2:1][C:2]1[C:3]([CH3:21])=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[C:7](=[O:14])[N:6]([CH2:15][CH2:16][N:17]([CH3:18])[CH3:19])[C:5]2=[O:20]

Participants

6

Reactant 3

HCID 887MethanolHCID 666867265-Amino-2-(2-(dimethylamino)ethyl)-4-methyl-6-nitroisoindoline-1,3-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 666871575,6-Diamino-2-(2-(dimethylamino)ethyl)-4-methylisoindoline-1,3-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 5-amino-2-(2-(dimethylamino)ethyl)-4-methyl-6-nitroisoindoline-1,3-dione (0.40 g, 1.37 mmol) in the mixture of methanol (8 mL) and acetic acid (0.4 mL) was added Pd/C (20 mg), and the resulting reaction mixture was hydrogenated for 2-3 h at 20-25 psi of hydrogen at rt. The reaction mixture was filtered through a pad of Celite and washed with methanol. The combined solvents were concentrated under vacuum to dryness. The crude product was used for the next step reaction without further purification. Mass (ESI, positive) m/z 263.0 [M+H]+.

Workup

  1. customthe resulting reaction mixture
  2. filtrationThe reaction mixture was filtered through a pad of Celite
  3. washwashed with methanol
  4. concentrationThe combined solvents were concentrated under vacuum to dryness
  5. customThe crude product was used for the next step reaction without further purification

Sources & evidence

ORD record
ord-cebb5bc68615496ba50da304fbcfc619
Source dataset
uspto-grants-2016_03
Patent number
US09273055B2

Reaction notes

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