1,5-Bis-(4-nitro-phenyl)-pentan-3-one → 1,5-Bis (4-amino-phenyl)-pentan-3-one

HRID 356478Notes

Reaction equation

HRID 356478 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12](=[O:24])[CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].C1COCC1>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12](=[O:24])[CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 187986641,5-Bis-(4-nitro-phenyl)-pentan-3-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 540520781,5-Bis (4-amino-phenyl)-pentan-3-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1,5-bis-(4-nitro-phenyl)-pentan-3-one from Example HH (9.00 g, 27.4 mmol), 5% Pd on BaSO4 (0.7 g), and THF (600 mL) was shaken in a hydrogen atmosphere of 52 psi at 26° C. for 17 hours. The catalyst was filtered, and the filtrate was concentrated. The residue was chromatographed on silica gel, eluting with 4% MeOH in CH2Cl2, to give the title compound. 1H NMR (CDCl3) δ 2.60 (m, 4 H), 2.74 (m, 4 H), 3.45 (bs, 4 H), 6.56 (m, 4 H), 6.91 (m, 4 H).

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was chromatographed on silica gel
  4. washeluting with 4% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-9eceef24e358448d86964a8b0b25887e
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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