9,10-Phenanthrenedione → HCID 136388344, compound

HRID 1266931Notes

Reaction equation

HRID 1266931 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:37][NH2:38])=[N:20][C:21]([O:31][CH2:32][C:33]([F:36])([F:35])[F:34])=[C:22]([Cl:30])[C:23]=1[O:24][CH2:25][C:26]([F:29])([F:28])[F:27]>C(O)(=O)C>[Cl:17][C:18]1[C:19]([N:37]=[N:38][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][C:21]([O:31][CH2:32][C:33]([F:36])([F:35])[F:34])=[C:22]([Cl:30])[C:23]=1[O:24][CH2:25][C:26]([F:27])([F:28])[F:29]

Participants

4

Reactant 2

HCID 67639,10-Phenanthrenedione2×HCID 18544802HCID 18544802, compound

Product 1

HCID 136388344HCID 136388344, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
105 °C

Procedure

Next, a reaction flask was loaded with acetic acid (30 ml) and 9,10-phenanthrenequinone (1.25 g), and the temperature was raised to 105° C. with stirring to dissolve 9,10-phenanthrenequinone. To this mixture, 3,5-dichloro-2-hydrazino-4,6-bis(2,2,2-trifluoroethoxy)pyridine (2.5 g) was added in 15 minutes. After stirring at 100 to 105° C. for two hours, the heating was stopped and the reaction mixture was left to cool and filtrated. The filtrated crystals were stirred for 30 minutes in methanol (100 ml), and then filtrated and dried to give intended crystals (2.3 g).

Workup

  1. stirringAfter stirring at 100 to 105° C. for two hours
  2. waitthe reaction mixture was left
  3. temperatureto cool
  4. filtrationfiltrated
  5. stirringThe filtrated crystals were stirred for 30 minutes in methanol (100 ml)
  6. filtrationfiltrated
  7. customdried
  8. customto give

Sources & evidence

ORD record
ord-4ce14a472e0640d99477585981d83f89
Source dataset
uspto-grants-2003_04
Patent number
US06551682B1

Reaction notes

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