9,10-Phenanthrenedione → 10-(3,5-Dichloro-2-pyridylazo)-9-phenanthrol

HRID 1266920

Reaction equation

HRID 1266920 reaction equation
[CH:1]1[C:14]2[C:13](=O)[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Cl:17][C:18]1[C:19]([NH:25][NH2:26])=[N:20][CH:21]=[C:22]([Cl:24])[CH:23]=1>C(O)(=O)C>[Cl:17][C:18]1[C:19]([N:25]=[N:26][C:13]2[C:14]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:12]=2[OH:16])=[N:20][CH:21]=[C:22]([Cl:24])[CH:23]=1

Participants

4

Reactant 2

HCID 67639,10-Phenanthrenedione2×HCID 6009663,5-Dichloro-2-hydrazinylpyridine

Product 1

HCID 13571850810-(3,5-Dichloro-2-pyridylazo)-9-phenanthrol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
105 °C

Procedure

Next, a reaction flask was loaded with acetic acid (15 ml) and 9,10-phenanthrenequinone (5.0 g), and the temperature was raised to 105° C. with stirring to dissolve 9,10-phenanthrenequinone. To the resultant, the crystals of 3,5-dichloro-2-hydrazinopyridine (4.6 g) was added in 30 minutes. After stirring at 105 to 110° C. for one hour, the reaction mixture was filtrated. The filtrated crystals were washed with methanol, and then dried to give intended crystals (5.1 g).

Workup

  1. stirringAfter stirring at 105 to 110° C. for one hour
  2. filtrationthe reaction mixture was filtrated
  3. washThe filtrated crystals were washed with methanol
  4. customdried
  5. customto give

Sources & evidence

ORD record
ord-5ffcf76dc5404586bdf823c8317970b4
Source dataset
uspto-grants-2003_04
Patent number
US06551682B1

Linked notes

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