HCID 86623818, compound → HCID 67506096, compound

HRID 1994654Notes

Reaction equation

HRID 1994654 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:11]2([C:44]3[CH:49]=[CH:48][C:47]([OH:50])=[C:46]([N+:51]([O-])=O)[CH:45]=3)[C:23]3[CH:22]=[C:21]([C:24]45[CH2:33][CH:28]6[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]6)[CH2:25]4)[CH2:31]5)[CH:20]=[CH:19][C:18]=3[C:17]3[C:12]2=[CH:13][C:14]([C:34]24[CH2:43][CH:38]5[CH2:39][CH:40]([CH2:42][CH:36]([CH2:37]5)[CH2:35]2)[CH2:41]4)=[CH:15][CH:16]=3)[CH:7]=[CH:8][C:9]=1[OH:10])([O-])=O>[Pd].CN(C)C=O>[NH2:1][C:4]1[CH:5]=[C:6]([C:11]2([C:44]3[CH:49]=[CH:48][C:47]([OH:50])=[C:46]([NH2:51])[CH:45]=3)[C:23]3[CH:22]=[C:21]([C:24]45[CH2:31][CH:30]6[CH2:32][CH:26]([CH2:27][CH:28]([CH2:29]6)[CH2:33]4)[CH2:25]5)[CH:20]=[CH:19][C:18]=3[C:17]3[C:12]2=[CH:13][C:14]([C:34]24[CH2:43][CH:38]5[CH2:39][CH:40]([CH2:42][CH:36]([CH2:37]5)[CH2:35]2)[CH2:41]4)=[CH:15][CH:16]=3)[CH:7]=[CH:8][C:9]=1[OH:10]

Participants

4

Reactant 1

HCID 86623818HCID 86623818, compound

Product 1

HCID 67506096HCID 67506096, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

Next, in a 300 mL recovery flask, 71.0 g of the obtained 9,9-bis(3-nitro-4-hydroxyphenyl)-2,7-di(1-adamantyl)-fluorene (0.10 mol), 0.318 g of 10% palladium-activated carbon (0.30 mmol), 273 mL of N,N-dimethylformamide and a stirrer were charged and agitated at 25° C. for 24 hours under a hydrogen atmosphere. A reaction solution was filtered and then added to 1 L of ion-exchange water. Solid precipitate was collected by filtration, then agitated in 1 L of ion-exchange water for one hour and dried under reduced pressure, thus obtaining 61.0 g of 9,9-bis(3-amino-4-hydroxy-phenyl)-2,7-di(1-adamantyl)-fluorene (0.094 mol; the yield was 94.0%).

Workup

  1. filtrationA reaction solution was filtered
  2. additionadded to 1 L of ion-exchange water
  3. filtrationSolid precipitate was collected by filtration
  4. stirringagitated in 1 L of ion-exchange water for one hour
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-43cd848d9354457e960d5467001b4f48
Source dataset
uspto-grants-2010_01
Patent number
US07652125B2

Reaction notes

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