N,N-Dimethylaniline → 5,12-dihydro-benzo[b]phenazine

HRID 895964Notes

Reaction equation

HRID 895964 reaction equation
O[C:2]1[C:11](O)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[C:13]1([NH2:20])[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH2:19].CN(C)C1C=CC=CC=1.C(Cl)Cl>C1(C)C=CC=CC=1.CCCCCCC>[CH:18]1[C:13]2[NH:20][C:11]3[CH:10]=[C:9]4[CH:8]=[CH:7][CH:6]=[CH:5][C:4]4=[CH:3][C:2]=3[NH:19][C:14]=2[CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 949N,N-DimethylanilineHCID 6344DichloromethaneHCID 70912,3-Dihydroxynaphthalene2×HCID 7243O-Phenylenediamine

Product 1

HCID 3523475,12-dihydro-benzo[b]phenazineYield 76%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8900HeptaneSolvent

Procedure

2,3-dihydroxynapthalene (10 g, 62.5 mmol), 1,2-phenylenediamine (6.75 g, 62.5 mmol) and N,N-dimethylaniline (54 ml) are placed into a round bottom flask under nitrogen atmosphere. Mixture is stirred at reflux. Reaction is monitored by TLC (CH2Cl2:Heptane/1:1) until all 2,3-dihydroxynaphthalene has reacted (˜3 hours). After cooling to room temperature, toluene (100 ml) is added and solid is collected by vacuum filtration. After washing with toluene (50 ml), ethanol (100 ml) and hexanes (50 ml), the product is dried under vacuum to yield 11.0 g (76% yield) of light yellow solid.

Workup

  1. temperatureat reflux
  2. customReaction
  3. customhas reacted (˜3 hours)
  4. filtrationsolid is collected by vacuum filtration
  5. washAfter washing with toluene (50 ml), ethanol (100 ml) and hexanes (50 ml)
  6. customthe product is dried under vacuum
  7. customto yield 11.0 g (76% yield) of light yellow solid

Sources & evidence

ORD record
ord-72553dac175d4c249ec39ffb81082647
Source dataset
uspto-grants-2005_07
Patent number
US06919140B2

Reaction notes

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