Acetic Acid → 1,3-Diisopropyldibenzo[b,d]furan-2-amine

HRID 1750905Notes

Reaction equation

HRID 1750905 reaction equation
[CH2:1]=[C:2]([CH:4]1[C:12]2[C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[O:9][C:8]=2[CH:7]=[CH:6][C:5]1(C(C)=C)[NH2:17])[CH3:3].[CH2:21](O)[CH3:22].[C:24](O)(=O)C>[Pd].[Pt]>[CH:2]([C:4]1[C:12]2[C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[O:9][C:8]=2[CH:7]=[C:6]([CH:21]([CH3:22])[CH3:24])[C:5]=1[NH2:17])([CH3:3])[CH3:1]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 702EthanolHCID 673712461,2-Di(prop-1-en-2-yl)dibenzo[b,d]furan-2-amine

Product 1

HCID 584009881,3-Diisopropyldibenzo[b,d]furan-2-amineYield 34%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 23939PlatinumCatalyst

Procedure

To a 500 mL Parr Hydrogenator bottle was added 1,2-di(prop-1-en-2-yl)dibenzo[b,d]furan-2-amine (19.1 g, 72.5 mmol), 10% palladium on carbon (5.7 g, 5.36 mmol), 5% platinum on carbon (5.7 g, 1.46 mmol), ethanol (180 mL), and acetic acid (20 mL). The mixture was hydrogenated on a Parr hydrogenator overnight. The reaction mixture was filtered through Celite and washed with dichloromethane. The filtrate was evaporated to brown oil. The oil was dissolved in dichloromethane, washed with 10% sodium hydroxide, dried over magnesium sulfate, filtered, evaporated to a brown oil. The oil was purified using a 200 g Varian column eluting with 10% ethyl acetate/hexanes. 6.55 g (34% yield) of product was obtained.

Workup

  1. customwas hydrogenated on a Parr hydrogenator overnight
  2. filtrationThe reaction mixture was filtered through Celite
  3. washwashed with dichloromethane
  4. customThe filtrate was evaporated to brown oil
  5. dissolutionThe oil was dissolved in dichloromethane
  6. washwashed with 10% sodium hydroxide
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated to a brown oil
  10. customThe oil was purified
  11. washeluting with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-8f30d146ede34b7db438dece54957b4e
Source dataset
uspto-grants-2015_10
Patent number
US09156870B2

Reaction notes

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