O-Phenylenediamine → HCID 135696396, compound

HRID 1748975Notes

Reaction equation

HRID 1748975 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[Br:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[OH:18])[CH:13]=O>CN(C=O)C>[NH:7]1[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[N:8]=[C:13]1[C:12]1[CH:15]=[CH:16][C:17]([OH:18])=[C:10]([Br:9])[CH:11]=1

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 763083-Bromo-4-hydroxybenzaldehyde

Product 1

HCID 135696396HCID 135696396, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a DMF (3 mL) solvent, a mixture including 1,2-phenylenediamine (100 mg, 0.92 mmol), 3-bromo-4-hydroxybenzaldehyde (187.8 mg, 0.92 mmol), and Na2S2O5 (177.6 mg, 0.92 mmol) was mixed at a temperature of 80° C. for 1 hour. After cooling, DMF was removed therefrom under reduced pressure. Methylene chloride and water were added thereto to obtain a solid product, and the precipitate was filtered, and the filtered product was washed with methylene chloride, ethyl acetate, and water to obtain a solid Compound 56 (79.4%).

Workup

  1. additionwas mixed at a temperature of 80° C. for 1 hour
  2. temperatureAfter cooling
  3. customDMF was removed
  4. additionMethylene chloride and water were added
  5. customto obtain a solid product
  6. filtrationthe precipitate was filtered
  7. washthe filtered product was washed with methylene chloride, ethyl acetate, and water

Sources & evidence

ORD record
ord-7d9adb7505484c23b64f4b380313e5de
Source dataset
uspto-grants-2015_10
Patent number
US09155690B2

Reaction notes

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