HCID 86623821, compound → HCID 67506199, compound

HRID 1994661Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

Next, in a 300 mL recovery flask, 29.1 g of the obtained 4,6-di(1-adamantyl)-1,3-bis(4-nitro-phenoxy)benzene (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 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 another one hour and dried under reduced pressure, thus obtaining 22.3 g of 4,6-di(1-adamantyl)-1,3-bis(4-amino-phenoxy)benzene (39.7 mmol; the yield was 84.9%).

Workup

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

Sources & evidence

ORD record: ord-4f40aedf649d4503b91535a83bd800ad
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652125B2

Reaction notes

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