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

HRID 1272471

Reaction equation

HRID 1272471 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:14]=[C:15]([C:19]([C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([OH:29])[CH:24]=2)=O)=O)[CH:16]=[CH:17][CH:18]=1>O1CCOCC1.O>[ClH:1].[ClH:1].[OH:12][C:13]1[CH:14]=[C:15]([C:19]2[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([OH:29])[CH:24]=3)=[N:10][C:4]3[C:3](=[CH:8][CH:7]=[C:6]([NH2:9])[CH:5]=3)[N:11]=2)[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 941791,2,4-Benzenetriamine, hydrochloride (1:2)HCID 13158606Bis(3-hydroxyphenyl)ethane-1,2-dione

Product 1

HCID 184556882,3-Bis(3-hydroxyphenyl)quinoxalin-6-ylamine dihydrochloride saltYield 168.5%

Reagents, catalysts & solvents 1

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

Procedure

40.4 mg (0.206 mmol) of 1,2,4-benzenetriamine dihydrochloride and 50 mg (0.20 mmol) of 3,3′-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 69.8 mg (92.6% yield) of the product. 97.6% purity by LC/MS (230 DAD). Mass-spec [ES+]=330.8. 1H NMR (500 MHz, MeOH-d4) 6.81–6.87 (2H, m), 6.96–6.98 (4H, m), 7.10 (1H, m), 7.13–7.16 (1H, t), 7.28–7.31 (1H, t), 7.56–7.58 (1H, m), 8.04–8.06 (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-d6cbecb797184468a35cd63732610dec
Source dataset
uspto-grants-2007_04
Patent number
US07208493B2

Linked notes

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