Tetrahydrofuran → 4-Amino-4'-octylbiphenyl

HRID 601449Notes

Reaction equation

HRID 601449 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-])=O.C1COCC1>[Pd].C(O)C>[CH2:16]([C:13]1[CH:14]=[CH:15][C:10]([C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)=[CH:11][CH:12]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 67059819HCID 67059819, compound

Product 1

HCID 52444204-Amino-4'-octylbiphenylYield 67%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4′-Nitro-4-n-octyl-biphenyl (1.2 g, 3.9 mmol) was added to a suspension of palladium on carbon (Pd/C, 1.0 g) in a mixed solvent of THF (60 mL) and ethanol (24 mL). The preparation was hydrogenized under constant hydrogen flow for 3 hours. The catalyst was filtered out, and the volatiles were removed in vacuo to give a pale yellow oil. Chromatography on silica gel gave 4-n-octyl-4′-amino-biphenyl as a colorless oil, which solidified upon standing (0.75 g, 67% yield).

Workup

  1. customfor 3 hours
  2. filtrationThe catalyst was filtered out
  3. customthe volatiles were removed in vacuo
  4. customto give a pale yellow oil

Sources & evidence

ORD record
ord-392a9e8d1abd429bb125bcd09ead2e94
Source dataset
uspto-grants-2011_03
Patent number
US07902363B2

Reaction notes

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