4-Nitro-N-methylphthalimide → 5-amino-2-methyl-2,3-dihydro-1H-isoindole-1,3-dione

HRID 2357055Notes

Reaction equation

HRID 2357055 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][C:9]([N+:12]([O-])=O)=[CH:10][CH:11]=[C:4]2[C:3]1=[O:15]>O>[NH2:12][C:9]1[CH:8]=[C:5]2[C:6](=[O:7])[N:2]([CH3:1])[C:3](=[O:15])[C:4]2=[CH:11][CH:10]=1

Participants

3

Reactant 1

HCID 923214-Nitro-N-methylphthalimide

Product 1

HCID 7269315-amino-2-methyl-2,3-dihydro-1H-isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of SnCl2 dihydrate (19.2 g, 85 mmol) in 8 ml water and 24 ml concentrated Hcl was added N-methyl-4-nitrophthalimide (4.5 g, 21.8 mmol). The mixture was stirred vigorously for 2 hours, and allowed to stand overnight. The mixture was then concentrated to ¾ original volume using rotavapor. The solid obtained was filtered and washed with water several times. The solid was dried to give 4-amino-N-methylphthalimide ((2.1 g (54.7%), Mp 247-248° C.).

Workup

  1. waitto stand overnight
  2. concentrationThe mixture was then concentrated
  3. customThe solid obtained
  4. filtrationwas filtered
  5. washwashed with water several times
  6. customThe solid was dried

Sources & evidence

ORD record
ord-71a4e85316aa43bb976cafda453df1fb
Source dataset
uspto-grants-2010_07
Patent number
US07759468B1

Reaction notes

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