Triethyl Phosphate → Dibenzocarbazole

HRID 1914408Notes

Reaction equation

HRID 1914408 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[C:11]2[C:16]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=3[CH:23]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)([O-])=O.P(OCC)(OCC)(OCC)=O>O>[CH:21]1[C:22]2[C:23]3[NH:1][C:4]4[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=4[C:10]=3[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:17]=2[CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 6535Triethyl PhosphateHCID 58410431HCID 58410431, compound

Product 1

HCID 155584DibenzocarbazoleYield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

Next, a mixed solution of 2.0 g of 9-(2-nitrophenyl)phenanthrene and 40 ml of triethyl phosphate was heated and stirred under a nitrogen gas stream at 150° C. for 8 hours. After cooling to room temperature, 50 ml of water was poured into the solution, followed by extraction with 50 ml of toluene. The organic layer was washed twice with 50 ml of water, dried over magnesium sulfate and then concentrated by evaporation. The concentrate was purified by silica gel chromatography and then vacuum-dried to obtain 840 mg of 13H-13-azaindeno[1,2-l]phenanthrene.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionfollowed by extraction with 50 ml of toluene
  3. washThe organic layer was washed twice with 50 ml of water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated by evaporation
  6. customThe concentrate was purified by silica gel chromatography
  7. customvacuum-dried

Sources & evidence

ORD record
ord-8ff2a2ba7d5c4f809a65fa3a6850152e
Source dataset
uspto-grants-2013_12
Patent number
US08610345B2

Reaction notes

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