HCID 22556140, compound → HCID 22556139, compound

HRID 1828614Notes

Reaction equation

HRID 1828614 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:41]([O:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][O:50][C:51]2[CH:56]=[CH:55][C:54]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)=[CH:53][CH:52]=2)=[O:42])[C:7]([C:10]2[C:11]([C:19]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]3[CH:34]=[CH:33][C:32]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[CH:31][CH:30]=3)=[O:20])=[CH:12][C:13]([N+:16]([O-])=O)=[CH:14][CH:15]=2)=[CH:8][CH:9]=1)([O-])=O>[Pd].O1CCCC1>[NH2:16][C:13]1[CH:12]=[C:11]([C:19]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]2[CH:30]=[CH:31][C:32]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=[CH:33][CH:34]=2)=[O:20])[C:10]([C:7]2[C:6]([C:41]([O:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][O:50][C:51]3[CH:56]=[CH:55][C:54]([C:57]4[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=4)=[CH:53][CH:52]=3)=[O:42])=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 1

HCID 22556140HCID 22556140, compound

Product 1

HCID 22556139HCID 22556139, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Bis{6-[4-biphenyloxy]hexyl} 4,4′-dinitro-2,2′-biphenyldicarboxylate (8) (2.26 g, 2.70 mol), palladium on activated carbon (5%, 0.31 g), and tetrahydrofuran (50 ml) were added to a hydrogenation bottle. The bottle was secured on a Parr hydrogenation apparatus, flushed five times with hydrogen, then pressurized with hydrogen to 56 psi. The pressure was maintained and the vessel was agitated for 24 hours. After the reaction mixture was filtered and about 100 ml of hexanes were added to recrystallize the products directly to afford 1.7 g (80%) of light yellow crystals. mp: 122–124° C. 1H-NMR (CDCl3) δ (ppm) 1.2–1.8 (m, 16H), 3.9 (m, 8H), 6.8–7.6 (m, 24H).

Workup

  1. customflushed five times with hydrogen
  2. temperatureThe pressure was maintained
  3. filtrationAfter the reaction mixture was filtered
  4. additionabout 100 ml of hexanes were added
  5. customto recrystallize the products directly
  6. customto afford 1.7 g (80%) of light yellow crystals

Sources & evidence

ORD record
ord-d2bc5248730f4a0cb89857cf4a43bcc8
Source dataset
uspto-grants-2006_06
Patent number
US07058249B2

Reaction notes

Loading…