2,4-Bis(isopropenyl)dibenzo[b,d]furan-3-amine → 2,4-Diisopropyldibenzo[b,d]furan-3-amine

HRID 1750899Notes

Reaction equation

HRID 1750899 reaction equation
[C:1]([C:4]1[C:16]([NH2:17])=[C:15]([C:18]([CH3:20])=[CH2:19])[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)([CH3:3])=[CH2:2]>C(O)C.[Pd].[Pt]>[CH:1]([C:4]1[C:16]([NH2:17])=[C:15]([CH:18]([CH3:20])[CH3:19])[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)([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 584008402,4-Bis(isopropenyl)dibenzo[b,d]furan-3-amine

Product 1

HCID 584009912,4-Diisopropyldibenzo[b,d]furan-3-amineYield 90%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

2,4-bis (isopropenyl)dibenzo[b,d]furan-3-amine (6.6 g, 25 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 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 6 g (90% yield) of desired product.

Workup

  1. waithydrogenated at 50 psi of H2 over night
  2. filtrationThe reaction mixture was filtered through a Celite pad
  3. washwashed with methylene chloride
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-a02d5dac62ac4cd293d6012483ca9c36
Source dataset
uspto-grants-2015_10
Patent number
US09156870B2

Reaction notes

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