Urea → 5-Amino-6-nitro-1H-isoindole-1,3(2H)-dione

HRID 920470

Reaction equation

HRID 920470 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:7](=[O:14])[NH:6][C:5]2=[O:15].[NH2:16]C(N)=O>O>[NH2:16][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:7](=[O:14])[NH:6][C:5]2=[O:15]

Participants

4

Reactant 2

HCID 1176UreaHCID 28011294-Chloro-5-nitrophthalimide

Product 1

HCID 151445685-Amino-6-nitro-1H-isoindole-1,3(2H)-dioneYield 92.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 5-chloro-6-nitroisoindoline-1,3-dione (28.0 g, 0.123 mol) and urea (73.8 g, 1.23 mol) was stirred and heated to 150° C. under argon for 6 h. After cooled to rt, the solid was suspended in hot water (100 mL, 80° C.), filtered, washed with hot water (3×50 mL) and dried under vacuum to give a yellow solid product, 23.56 g, 92.5% yield.

Workup

  1. temperatureAfter cooled to rt
  2. filtrationfiltered
  3. washwashed with hot water (3×50 mL)
  4. customdried under vacuum
  5. customto give a yellow solid product, 23.56 g, 92.5% yield

Sources & evidence

ORD record
ord-ed47e73b7daf467f93712a427a8e6c1c
Source dataset
uspto-grants-2016_03
Patent number
US09273055B2

Linked notes

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