1H-Isoindole-1,3(2H)-dione, 2-methyl-4-nitro- → 4-amino-2-methyl-2,3-dihydro-1H-isoindole-1,3-dione

HRID 48223Notes

Reaction equation

HRID 48223 reaction equation
[CH3:1][N:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N+:12]([O-])=O)[C:3]1=[O:15].[H][H]>[Pd].C(O)(=O)C>[NH2:12][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[C:10](=[O:11])[N:2]([CH3:1])[C:3]2=[O:15]

Participants

5

Reactant 2

HCID 757721H-Isoindole-1,3(2H)-dione, 2-methyl-4-nitro-HCID 178418361HCID 178418361, compound

Product 1

HCID 6005964-amino-2-methyl-2,3-dihydro-1H-isoindole-1,3-dioneYield 181.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A pressure reactor was charged with 2-methyl-4-nitro-1H-isoindole-1,3(2H)-dione (59.0 g, 0.286 mol), 1 L acetic acid, and 2 q 5% Pd/C. The reactor was pressurized to 48 psi hydrogen, and the exothermic reaction was complete in 2 hours. The catalyst was removed with hot filtration, and the filtrate combined with the contents of another reactor which contained 53.2 g of 3-nitrophthalimide under the same conditions. The acetic acid was removed at the rotovap, then the salt was cracked by adding 2 M ammonium hydroxide. The slurry was stirred 30 minutes; then filtered; washed with water, ethanol, and ether; and dried at the pump to give 91.4 g, 95% of the product.

Workup

  1. customthe exothermic reaction
  2. customThe catalyst was removed with hot filtration
  3. customthe filtrate combined with the contents of another reactor
  4. customThe acetic acid was removed at the rotovap
  5. additionby adding 2 M ammonium hydroxide
  6. filtrationthen filtered
  7. washwashed with water, ethanol, and ether
  8. customand dried at the pump

Sources & evidence

ORD record
ord-1ea7119dde9341f88c5120ddc594b09b
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Reaction notes

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