O-Phenylenediamine → HCID 370919, compound

HRID 452371Notes

Reaction equation

HRID 452371 reaction equation
[CH:1]([C:3]1[C:4](=[O:13])[NH:5][C:6]2[C:12]=1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=O.[C:14]1([NH2:21])[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH2:20].S(=O)(O)[O-].[Na+]>C(O)C.O>[N:20]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[NH:21][C:1]=1[C:3]1[C:4](=[O:13])[NH:5][C:6]2[C:12]=1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

6

Reactant 3

HCID 7243O-PhenylenediamineHCID 100350681,2-Dihydro-2-oxocyclohepta[b]pyrrole-3-carboxaldehydeHCID 23665763Sodium Bisulfite

Product 1

HCID 370919HCID 370919, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

3-Formyl-1-azaazulen-2-one (0.1 mmol) was dissolved in a mixture of 10 mL ethanol and 5 mL water. o-Phenylenediamine (0.15 mmol) and sodium bisulfite (0.2 mmol) were then added and heat to reflux for 1 day. After working up, the residue was then purified by column chromatography to give 8.6 mg of A1, yield 95%.

Workup

  1. temperatureheat
  2. temperatureto reflux for 1 day
  3. customthe residue was then purified by column chromatography

Sources & evidence

ORD record
ord-27e5d7a3657c45c3a61bb8a7c20df659
Source dataset
uspto-grants-2013_07
Patent number
US08492374B2

Reaction notes

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