3,4-Diaminobenzoic acid → HCID 74223924, compound

HRID 2205094Notes

Reaction equation

HRID 2205094 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=O)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=O.[NH2:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=1[NH2:26])[C:20]([OH:22])=[O:21]>CC(O)=O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:16][C:17]2[C:25](=[CH:24][CH:23]=[C:19]([C:20]([OH:22])=[O:21])[CH:18]=2)[N:26]=1

Participants

4

Reactant 2

HCID 692633,4-Diaminobenzoic acidHCID 275008Benzoyl-furoyl

Product 1

HCID 74223924HCID 74223924, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1-(furan-2-yl)-2-phenylethane-1,2-dione (100 mg, 0.50 mmol, 1.00 equiv) and 3,4-diaminobenzoic acid (76 mg, 0.50 mmol, 1.00 equiv) in AcOH (3 mL) was stirred under reflux for 3 hrs in a 50-mL round-bottom flask. The resulting mixture was concentrated under vacuum, quenched with water. Solids were collected by filtration affording 43 mg (27%) of 2-(furan-2-yl)-3-phenylquinoxaline-6-carboxylic acid as a grey solid.

Workup

  1. temperatureunder reflux for 3 hrs in a 50-mL round-bottom flask
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. customquenched with water
  4. filtrationSolids were collected by filtration

Sources & evidence

ORD record
ord-ef74b947a6e04bdba38c97717c32e62a
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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