HCID 19959520, compound → 4-Pyrrolidino-2-naphthol

HRID 54606Notes

Reaction equation

HRID 54606 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:4][C:3]=1[OH:17].[H][H]>[OH-].[K+].[Pd]>[N:12]1([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:2]=[C:3]([OH:17])[CH:4]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 19959520HCID 19959520, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 199595214-Pyrrolidino-2-naphthol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 14797Potassium HydroxideSolvent

Procedure

1-Chloro-4-pyrrolidino-2-naphthol (2.47 g;0.010 mol), prepared as described in Example 6(a), was dissolved in 10% aqueous potassium hydroxide (50 ml) and was treated in the presence of palladium on charcoal (1.00 g;5%) at room temperature under 3 atmospheres of hydrogen until a stoichiometric amount of hydrogen was absorbed (approximately 24h). The palladium catalyst was removed by filtration and the filtrate neutralised with glacial acetic acid. The solution was extracted with dichloromethane (2×50 ml), the extracts combined, dried and evaporated to afford crude 4-pyrrolidino-2-naphthol as an unstable dark oil (0.58 g;27%). The crude product could not be purified further using conventional methods. ##STR28##

Workup

  1. customwas absorbed (approximately 24h)
  2. customThe palladium catalyst was removed by filtration
  3. extractionThe solution was extracted with dichloromethane (2×50 ml)
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-ae22811d25d741f7903c686c159a8dd1
Source dataset
uspto-grants-1997_04
Patent number
US05623005

Reaction notes

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