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

HRID 561898Notes

Reaction equation

HRID 561898 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)-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

The following procedure is our modification: 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 at 150° C. for 6 h. Then the temperature was reduced to 90° C., water (400 mL) was added, the mixture was stirred overnight at RT. Precipitate was collected by filtration, water (300 mL) was added and stirred for 4 h at 95° C. The solid was collected by filtration and dried under vacuum. Yellow solid, 19.6 g (94.7 mmol, 77%). LCMS [M−H]− 205.9. 1H NMR (300 MHz, DMSO): δ 11.46 (s, 1H), 8.35 (s, 2H), 8.37 (s, 1H), 7.40 (s, 1H).

Workup

  1. customwas reduced to 90° C.
  2. stirringthe mixture was stirred overnight at RT
  3. filtrationPrecipitate was collected by filtration, water (300 mL)
  4. additionwas added
  5. stirringstirred for 4 h at 95° C
  6. filtrationThe solid was collected by filtration
  7. customdried under vacuum

Sources & evidence

ORD record
ord-df5ffcf802864f00a5414048bd10cd11
Source dataset
uspto-grants-2011_11
Patent number
US08063225B2

Reaction notes

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