O-Phenylenediamine → HCID 2917733, compound

HRID 350679Notes

Reaction equation

HRID 350679 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[C:9]1(=[O:15])[NH:13][C:12](=[O:14])[CH:11]=[CH:10]1>O.CO>[O:15]=[C:9]1[NH:8][C:1]2[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=2)[NH:7][CH:10]1[CH2:11][C:12]([NH2:13])=[O:14]

Participants

5

Reactant 2

HCID 7243O-PhenylenediamineHCID 10935Maleimide

Product 1

HCID 2917733HCID 2917733, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 1,2-phenylenediamine (21.5 g, 0.2 mol) in water (450 mL) was added dropwise a solution of maleimide, (20.0 g, 0.2 mol) in methanol (180 mL) over 60 min. The mixture was then stirred at 95° C. for 2 hours followed at rt overnight. The precipitate was collected via filtration and was washed with small amount of water for a few times to yield the title compound as a pale gray solid (pure product): 1H NMR (DMSO-d6) δ=10.2 (bs, 1H), 7.37 (bs, 1H) 6.88 (bs, 1H), 6.74–6.68 (m, 3H), 6.31–6.57 (m, 1H), 5.78 (bs, 1H), 4.08–4.04 (m, 1H), 2.63 (dd, 1H, J=3.6, 15.5 Hz), 2.32 (dd, 1H, J=3.3, 15.5 Hz); HPLC (CH3CN—H2O-0.1% TFA): Rf=9.49 min.

Workup

  1. waitfollowed at rt overnight
  2. filtrationThe precipitate was collected via filtration
  3. washwas washed with small amount of water for a few times

Sources & evidence

ORD record
ord-429beda41e61449288857d21e32aef49
Source dataset
uspto-grants-2007_02
Patent number
US07183281B2

Reaction notes

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