1,2,4-Benzenetriamine, hydrochloride (1:2) → 2,3-Bis(4-hydroxyphenyl)quinoxalin-6-ylamine Dihydrochloride

HRID 1272472

Reaction equation

HRID 1272472 reaction equation
[ClH:1].Cl.[C:3]1([NH2:11])[C:4]([NH2:10])=[CH:5][C:6]([NH2:9])=[CH:7][CH:8]=1.[OH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([C:21]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)=O)=O)=[CH:15][CH:14]=1>O1CCOCC1.O>[ClH:1].[ClH:1].[OH:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[C:21]([C:23]3[CH:24]=[CH:25][C:26]([OH:29])=[CH:27][CH:28]=3)=[N:10][C:4]3[C:3](=[CH:8][CH:7]=[C:6]([NH2:9])[CH:5]=3)[N:11]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 941791,2,4-Benzenetriamine, hydrochloride (1:2)HCID 4582044,4'-Dihydroxybenzil

Product 1

HCID 1356100782,3-Bis(4-hydroxyphenyl)quinoxalin-6-ylamine DihydrochlorideYield 167.3%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

98.04 mg (0.5 mmol) of 1,2,4-benzenetriamine dihydrochloride and 121.2 mg (0.5 mmol) of 4,4′-dihydroxybenzil were dissolved in 2 ml of 1:1 mixture of dioxane-water. The reaction was refluxed for 3 hours. Then solvent was removed in vacuo. The residue was dissolved in 2 ml of methanol and this solution was added dropwise to 40 ml of diethyl ether. The formed dark-red precipitate was collected, washed with ether and dried in vacuo to give 168.3 mg (83.7% yield) of the product. 98.7% purity by LC/MS (230 DAD). Mass-spec [ES+]=330.8. 1H NMR (500 MHz, MeOH-d4) 6.76–6.77 (2H, d), 6.87–6.89 (2H, d), 7.05–7.06 (1H, d), 7.29–7.31 (2H, d), 7.38–7.40 (2H, d), 7.50–7.52 (1H, m), 7.99–8.01 (1H, d).

Workup

  1. temperatureThe reaction was refluxed for 3 hours
  2. customThen solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in 2 ml of methanol
  4. additionthis solution was added dropwise to 40 ml of diethyl ether
  5. customThe formed dark-red precipitate was collected
  6. washwashed with ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-930be883949d4e908b6e89054035383d
Source dataset
uspto-grants-2007_04
Patent number
US07208493B2

Linked notes

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