Glyoxal → HCID 19101917, compound

HRID 1974663Notes

Reaction equation

HRID 1974663 reaction equation
N[C:2]1[C:11]([NH2:12])=[CH:10][CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[C:3]=1[C:13]([O:15][CH3:16])=[O:14].C(C=O)=O.O1C[CH2:24][CH2:23][CH2:22]1>O>[N:12]1[C:11]2[C:2](=[C:3]([C:13]([O:15][CH3:16])=[O:14])[C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:9][CH:10]=2)[CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7860GlyoxalHCID 8028TetrahydrofuranHCID 145744761,2-Benzenedicarboxylic acid, 3,4-diamino-, 1,2-dimethyl ester

Product 1

HCID 19101917HCID 19101917, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of dimethyl 3,4-diaminophthalate (11.2 g, 0.05 mol) in tetrahydrofuran is treated with glyoxal (2.9 g, 0.05 mol) in water at reflux temperature, stirred for 4 hours at reflux temperature and overnight at room temperature, and concentrated in vacuo. The resultant residue is partitioned between water and methylene chloride. The organic phase is dried (MgSO4) and concentrated in vacuo to give a brown solid residue. Recrystallization from methanol gives the title product as a pink powder (9.67 g, 78.6%) mp 124°-125° C., identified by H1NMR, C13NMR, and IR spectral analyses.

Workup

  1. temperatureat reflux temperature
  2. concentrationconcentrated in vacuo
  3. customThe resultant residue is partitioned between water and methylene chloride
  4. dry with materialThe organic phase is dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give a brown solid residue
  7. customRecrystallization from methanol

Sources & evidence

ORD record
ord-c952ba58284f4fbabd0a85edd5a32a67
Source dataset
uspto-grants-1994_02
Patent number
US05283335

Reaction notes

Loading…