9,10-Phenanthrenedione → 10-[3-Chloro-5-(trifluoro-methyl)-2-pyridylazo]-9-phenanthrol

HRID 1266918

Reaction equation

HRID 1266918 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:28][NH2:29])=[N:20][CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1>C(O)(=O)C>[Cl:17][C:18]1[C:19]([N:28]=[N:29][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]([C:24]([F:27])([F:25])[F:26])[CH:23]=1

Participants

4

Reactant 2

HCID 67639,10-Phenanthrenedione2×HCID 12726913-Chloro-2-hydrazinyl-5-(trifluoromethyl)pyridine

Product 1

HCID 13571851310-[3-Chloro-5-(trifluoro-methyl)-2-pyridylazo]-9-phenanthrol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °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 100° C. with stirring to dissolve 9,10-phenanthrenequinone. To the resultant, the crystals of 3-chloro-2-hydrazino-5-(trifluoromethyl)-pyridine (5.0 g) was added in 30 minutes. After stirring at 100 to 105° C. for one hour, the reaction mixture was filtrated. After being washed with methanol, the obtained crystals were dried to give intended crystals (5.6 g).

Workup

  1. stirringAfter stirring at 100 to 105° C. for one hour
  2. filtrationthe reaction mixture was filtrated
  3. washAfter being washed with methanol
  4. customthe obtained crystals were dried
  5. customto give

Sources & evidence

ORD record
ord-d13af6f1ad5747ef991459ec5268d43d
Source dataset
uspto-grants-2003_04
Patent number
US06551682B1

Linked notes

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