9,10-Phenanthrenedione → 10-[6-(2,2,3,3,4,4,5,5-Octafluoropentyloxy)-2-pyridylazo]-9-phenanthrol

HRID 1266926

Reaction equation

HRID 1266926 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.[NH:17]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][C:27]([F:38])([F:37])[C:28]([F:36])([F:35])[C:29]([F:34])([F:33])[CH:30]([F:32])[F:31])[N:20]=1)[NH2:18]>C(O)(=O)C>[F:38][C:27]([F:37])([C:28]([F:35])([F:36])[C:29]([F:33])([F:34])[CH:30]([F:32])[F:31])[CH2:26][O:25][C:21]1[N:20]=[C:19]([N:17]=[N:18][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])[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 67639,10-Phenanthrenedione2×HCID 185447822-Hydrazino-6-(2,2,3,3,4,4,5,5-octafluoropentyloxy)pyridine

Product 1

HCID 13638834310-[6-(2,2,3,3,4,4,5,5-Octafluoropentyloxy)-2-pyridylazo]-9-phenanthrol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

Next, a reaction flask was loaded with acetic acid (54 ml) and 9,10-phenanthrenequinone (3.8 g), and the temperature was raised to 110° C. with stirring to dissolve 9,10-phenanthrenequinone. To this mixture, 2-hydrazino-6-(2,2,3,3,4,4,5,5-octafluoropentyloxy)pyridine (10 g) was added in 30 minutes. After stirring at 110° C. for one hour, the reaction mixture was filtrated. Crystals were stirred in methanol (100 ml) for 30 minutes, filtrated and dried to give intended crystals (5.2 g).

Workup

  1. stirringAfter stirring at 110° C. for one hour
  2. filtrationthe reaction mixture was filtrated
  3. stirringCrystals were stirred in methanol (100 ml) for 30 minutes
  4. filtrationfiltrated
  5. customdried
  6. customto give

Sources & evidence

ORD record
ord-65e0b6deb2c2449c93641d4701329184
Source dataset
uspto-grants-2003_04
Patent number
US06551682B1

Linked notes

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