HCID 87489742, compound → HCID 68539428, compound

HRID 1994656Notes

Reaction equation

HRID 1994656 reaction equation
[OH:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([C:11]23[CH2:20][CH:15]4[CH2:16][CH:17]([CH2:19][C:13]([C:21]56[CH2:30][CH:25]7[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]7)[CH2:22]5)[CH2:28]6)([CH2:14]4)[CH2:12]2)[CH2:18]3)=[CH:4][C:3]=1[C:31]1[CH:36]=[C:35]([C:37]23[CH2:46][CH:41]4[CH2:42][CH:43]([CH2:45][C:39]([C:47]56[CH2:56][CH:51]7[CH2:52][CH:53]([CH2:55][CH:49]([CH2:50]7)[CH2:48]5)[CH2:54]6)([CH2:40]4)[CH2:38]2)[CH2:44]3)[CH:34]=[C:33]([N+:57]([O-])=O)[C:32]=1[OH:60]>[Pd].CN(C)C=O>[OH:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([C:11]23[CH2:20][CH:15]4[CH2:16][CH:17]([CH2:19][C:13]([C:21]56[CH2:22][CH:23]7[CH2:24][CH:25]([CH2:26][CH:27]([CH2:29]7)[CH2:28]5)[CH2:30]6)([CH2:14]4)[CH2:12]2)[CH2:18]3)=[CH:4][C:3]=1[C:31]1[CH:36]=[C:35]([C:37]23[CH2:46][CH:41]4[CH2:42][CH:43]([CH2:45][C:39]([C:47]56[CH2:48][CH:49]7[CH2:55][CH:53]([CH2:52][CH:51]([CH2:50]7)[CH2:56]5)[CH2:54]6)([CH2:40]4)[CH2:38]2)[CH2:44]3)[CH:34]=[C:33]([NH2:57])[C:32]=1[OH:60]

Participants

4

Reactant 1

HCID 87489742HCID 87489742, compound

Product 1

HCID 68539428HCID 68539428, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

Next, in a 300 mL recovery flask, the obtained 81.3 g of 2,2′-dihydroxy-3,3′-dinitro-5,5′-bis[3-(1-adamantyl)-(1-adamantyl)]-biphenyl (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 69.3 g of 2,2′-dihydroxy-3,3′-diamino-5,5′-bis[3-(1-adamantyl)-(1-adamantyl)]-biphenyl (0.092 mol; the yield was 92.0%).

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-3a55f378cb0d4721a08c2b395f3b9a44
Source dataset
uspto-grants-2010_01
Patent number
US07652125B2

Reaction notes

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