Ethanol → 2-Propyl-3-phenyl-7-amino-1-naphthol

HRID 128005Notes

Reaction equation

HRID 128005 reaction equation
[CH2:1]([C:4]1[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:12][C:11]2[C:6](=[CH:7][C:8]([N+:20]([O-])=O)=[CH:9][CH:10]=2)[C:5]=1[OH:23])[CH:2]=[CH2:3].C(O)C.[H][H]>CC(C)=O.[Pd]>[CH2:1]([C:4]1[C:13]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:12][C:11]2[C:6](=[CH:7][C:8]([NH2:20])=[CH:9][CH:10]=2)[C:5]=1[OH:23])[CH2:2][CH3:3]

Participants

6

Reactant 3

HCID 702EthanolHCID 202396582-Allyl-3-phenyl-7-nitro-1-naphtholHCID 178418361HCID 178418361, compound

Product 1

HCID 202396562-Propyl-3-phenyl-7-amino-1-naphthol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 180AcetoneSolvent

Procedure

14 g of 2-Allyl-3-phenyl-7-nitro-1-naphthol prepared in step (4) were dissolved in 200 ml of acetone. 300 ml of ethanol and one pinchful of a 10% palladium on charcoal catalyst were added. The resulting mixture was hydrogenated at room pressure and temperature until the theoretical amount of hydrogen was absorbed. The catalyst was then removed by filtration and the residual solution was evaporated to dryness under reduced pressure. The resulting crystals were washed with petroleum ether, filtered off and dried under sulfuric vacuum.

Workup

  1. customwas absorbed
  2. customThe catalyst was then removed by filtration
  3. customthe residual solution was evaporated to dryness under reduced pressure
  4. washThe resulting crystals were washed with petroleum ether
  5. filtrationfiltered off
  6. customdried under sulfuric vacuum

Sources & evidence

ORD record
ord-ab13e434b2dc48bfbc9b6362e747b61b
Source dataset
uspto-grants-1981_03
Patent number
US04258120

Reaction notes

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