Benzene → HCID 136045313, compound

HRID 1589138Notes

Reaction equation

HRID 1589138 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH3:19])[C:6]2[C:15]([CH:16]=1)=[N:14][C:13]1[C:8](=[CH:9][CH:10]=[CH:11][C:12]=1[O:17]C)[N:7]=2.[Cl-].[Cl-].[Cl-].[Al+3].C1C=CC=CC=1>C1(C)C=CC=CC=1.CC(C)=O>[CH3:19][C:5]1[CH:4]=[C:3]([OH:2])[CH:16]=[C:15]2[C:6]=1[N:7]=[C:8]1[C:13](=[N:14]2)[C:12]([OH:17])=[CH:11][CH:10]=[CH:9]1

Participants

5

Reactant 3

HCID 241BenzeneHCID 6451240Aluminum(III) ChlorideHCID 20248128HCID 20248128, compound

Product 1

HCID 136045313HCID 136045313, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 20247278Toluene acetoneSolvent

Procedure

A magnetically stirred mixture of 0.509 g (2 mmol) of 3.6-dimethoxy-1-methylphenazine, 1.0 g of aluminum trichloride (7.5 mmol), and 20 ml of benzene was heated at reflux for 18 hours. The mixture was cooled to room temperature and the solvent was removed on a rotary evaporator. The residue was treated with crushed ice and the resulting mixture was taken up in 1N sodium hydroxide and washed with dichloromethane. The combined dichloromethane layers were back-extracted with 1N sodium hydroxide and the combined aqueous layers were acidified to pH 4-5. The solution was extracted with dichloromethane containing a trace of methanol. The combined organic layers were washed with brine and dried over magnesium sulfate. The solvent was was stripped to yield 1.06 g of a brown and yellow solid mixture. Flash chromatography in 6:1 toluene-acetone yielded 0.38 g of a yellow solid. This was recrystallized from toluene to yield 298 mg of orange crystals; decomposition at >256° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. customthe solvent was removed on a rotary evaporator
  4. additionThe residue was treated with crushed ice
  5. washwashed with dichloromethane
  6. extractionThe combined dichloromethane layers were back-extracted with 1N sodium hydroxide
  7. extractionThe solution was extracted with dichloromethane containing a trace of methanol
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over magnesium sulfate
  10. customto yield 1.06 g of a brown and yellow solid mixture

Sources & evidence

ORD record
ord-23fd0ed7be024f4dabba8ab9072e3818
Source dataset
uspto-grants-1986_02
Patent number
US04568675

Reaction notes

Loading…