Urea → 5-Amino-2-methyl-6-nitroisoindoline-1,3-dione

HRID 920503Notes

Reaction equation

HRID 920503 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])[N:6]([CH3:15])[C:5]2=[O:16].[NH2:17]C(N)=O>>[NH2:17][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])[N:6]([CH3:15])[C:5]2=[O:16]

Participants

3

Reactant 2

HCID 1176UreaHCID 542627675-Chloro-2-methyl-6-nitroisoindoline-1,3-dione

Product 1

HCID 666871895-Amino-2-methyl-6-nitroisoindoline-1,3-dioneYield 66.1%

Conditions

Temperature
150 °C

Procedure

5-Chloro-2-methyl-6-nitroisoindoline-1,3-dione (14.40 g, 59.85 mmol) and urea (35.95 g, 599 mmol) were mixed together under argon. The mixture was stirred and heated to 150° C. for 3 h and cooled to rt. The solid was washed with 200 mL of hot water (90° C.) and filtered to remove the remaining urea. The isolated yellow solid was washed twice with hot water, dried under vacuum and purified by column chromatography (silica-gel CH2Cl2/acetone=19/1 v/v) to give a yellow solid product, 8.75 g, 66.1% yield. MS: 219.6 [M−H]−. 1H NMR (DMSO-d6, 500 MHz): δ 8.39 (s, 2H), 8.26 (s, 1H), 7.40 (s, 1H), 2.99 (s, 3H).

Workup

  1. temperaturecooled to rt
  2. washThe solid was washed with 200 mL of hot water (90° C.)
  3. filtrationfiltered
  4. customto remove the remaining urea
  5. washThe isolated yellow solid was washed twice with hot water
  6. customdried under vacuum
  7. custompurified by column chromatography (silica-gel CH2Cl2/acetone=19/1 v/v)
  8. customto give a yellow solid product, 8.75 g, 66.1% yield

Sources & evidence

ORD record
ord-f0891390f58847baaccec0fa45fbff69
Source dataset
uspto-grants-2016_03
Patent number
US09273055B2

Reaction notes

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