HCID 86623819, compound → HCID 67506048, compound

HRID 1994655Notes

Reaction equation

HRID 1994655 reaction equation
[N+:1]([C:4]1[CH:73]=[CH:72][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3([C:48]4[CH:53]=[CH:52][C:51]([O:54][C:55]5[CH:60]=[CH:59][C:58]([N+:61]([O-])=O)=[C:57]([O:64]CC6C=CC=CC=6)[CH:56]=5)=[CH:50][CH:49]=4)[C:27]4[CH:26]=[C:25]([C:28]56[CH2:37][CH:32]7[CH2:33][CH:34]([CH2:36][CH:30]([CH2:31]7)[CH2:29]5)[CH2:35]6)[CH:24]=[CH:23][C:22]=4[C:21]4[C:16]3=[CH:17][C:18]([C:38]35[CH2:47][CH:42]6[CH2:43][CH:44]([CH2:46][CH:40]([CH2:41]6)[CH2:39]3)[CH2:45]5)=[CH:19][CH:20]=4)=[CH:11][CH:10]=2)=[CH:6][C:5]=1[O:74]CC1C=CC=CC=1)([O-])=O>[Pd].CN(C)C=O>[OH:64][C:57]1[CH:56]=[C:55]([CH:60]=[CH:59][C:58]=1[NH2:61])[O:54][C:51]1[CH:52]=[CH:53][C:48]([C:15]2([C:12]3[CH:13]=[CH:14][C:9]([O:8][C:7]4[CH:72]=[CH:73][C:4]([NH2:1])=[C:5]([OH:74])[CH:6]=4)=[CH:10][CH:11]=3)[C:16]3[CH:17]=[C:18]([C:38]45[CH2:45][CH:44]6[CH2:46][CH:40]([CH2:41][CH:42]([CH2:43]6)[CH2:47]4)[CH2:39]5)[CH:19]=[CH:20][C:21]=3[C:22]3[C:27]2=[CH:26][C:25]([C:28]24[CH2:29][CH:30]5[CH2:36][CH:34]([CH2:33][CH:32]([CH2:31]5)[CH2:37]2)[CH2:35]4)=[CH:24][CH:23]=3)=[CH:49][CH:50]=1

Participants

4

Reactant 1

HCID 86623819HCID 86623819, compound

Product 1

HCID 67506048HCID 67506048, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

Next, 50.2 g of the obtained 9,9-bis[4-(4-nitro-3-benzyloxyphenoxy)-phenyl]-2,7-di(1-adamantyl)-fluorene (46.8 mmol), 1.49 g of 10% palladium-activated carbon (1.40 mmol), 273 mL of N,N-dimethylformamide and a stirrer were charged in a 300 mL recovery flask and agitated at 25° C. for 24 hours under a hydrogen atmosphere. A reaction solution was filtered and then added to in 1 L of ion-exchange water. Solid precipitate was collected by filtration, then agitated in 1 L of ion-exchange water for another one hour and dried under reduced pressure, thus obtaining 34.6 g of 9,9-bis[4-(3-hydroxy-4-amino-phenoxy)-phenyl]-2,7-di(1-adamantyl)-fluorene (41.5 mmol; the yield was 88.7%).

Workup

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

Sources & evidence

ORD record
ord-fc60f89f4a514a3d9c9bf56d4541e71c
Source dataset
uspto-grants-2010_01
Patent number
US07652125B2

Reaction notes

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