2,4-Bis(2-methylprop-1-enyl)dibenzo[b,d]furan-3-amine → 2,4-Diisobutyldibenzofuran-3-amine

HRID 1750924Notes

Reaction equation

HRID 1750924 reaction equation
[CH3:1][C:2]([CH3:22])=[CH:3][C:4]1[C:16]([NH2:17])=[C:15]([CH:18]=[C:19]([CH3:21])[CH3:20])[C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=1>C(O)C.[Pd].[Pt]>[CH2:3]([C:4]1[C:16]([NH2:17])=[C:15]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=1)[CH:2]([CH3:22])[CH3:1]

Participants

5

Reactant 1

HCID 584009782,4-Bis(2-methylprop-1-enyl)dibenzo[b,d]furan-3-amine

Product 1

HCID 584010632,4-Diisobutyldibenzofuran-3-amineYield 96%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

2,4-bis(2-methylprop-1-enyl)dibenzo[b,d]furan-3-amine (5.45 g, 18.7 mmol) was dissolved in ethanol (150 mL) and to it were added 10% Pd/C (1.5 g) and 5% Pt/C (1.5 g) and hydrogenated at 50 psi of H2 for over night. GC indicated complete conversion of olefin to alkane. The reaction mixture was filtered through a Celite pad and washed with methylene chloride. The filtrate was concentrated to produce 5.3 g (96% yield) of desired product.

Workup

  1. filtrationThe reaction mixture was filtered through a Celite pad
  2. washwashed with methylene chloride
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-028748d870e34f07b973b17eaaaf2eec
Source dataset
uspto-grants-2015_10
Patent number
US09156870B2

Reaction notes

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