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

HRID 69356Notes

Reaction equation

HRID 69356 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-bb729edd0d0f4e12bb8825967655bbd4
Source dataset
uspto-grants-2014_09
Patent number
US08822500B2

Reaction notes

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