Ethanol → 5,12-Dihydroquinoxalino[2,3-b]phenazine

HRID 2272924Notes

Reaction equation

HRID 2272924 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[CH2:9](O)[CH3:10]>C(O)C1C=CC=CC=1>[CH:6]1[C:1]2[NH:8][C:9]3[C:10](=[CH:6][C:1]4[C:2]([CH:3]=3)=[N:8][C:1]3[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:7]=4)[NH:7][C:2]=2[CH:3]=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 7243O-Phenylenediamine

Product 1

HCID 41665265,12-Dihydroquinoxalino[2,3-b]phenazineYield 92%

Reagents, catalysts & solvents 1

HCID 244Benzyl AlcoholSolvent

Conditions

Temperature
137.5 °C

Procedure

2,5-Dihydroxy-1,4-dibenzoquinone (4, 30.0 g, 0.2 mol) was added to a solution of o-phenylendiamine (5, 115.79 g, 1.1 mol) in benzyl alcohol (11.6 vol). The reaction mixture was heated to 135-140° C. and stirred for 20 hours. The reaction mixture was cooled to room temperature, and ethanol (120 mL) was added. The resulting suspension was filtered through a Buchner funnel and the solid was washed with ethanol (120 mL) and dried under vacuum in an oven at 60-70° C. to furnish 5,14-Dihydro-5,7,12,14-tetraazapentacene 3. Yield: 92%; HPLC purity: 99.56%.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe resulting suspension was filtered through a Buchner funnel
  3. washthe solid was washed with ethanol (120 mL)
  4. customdried under vacuum in an oven at 60-70° C.

Sources & evidence

ORD record
ord-d03e9a53cc3442a3a7b0db4fe922b289
Source dataset
uspto-grants-2015_09
Patent number
US09120803B2

Reaction notes

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