HCID 136404568, compound → HCID 68792857, compound

HRID 1695561Notes

Reaction equation

HRID 1695561 reaction equation
[H][H].[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[C:13]1[C:25]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18](=[N:26]O)[C:17]=2[CH:16]=[CH:15][CH:14]=1>C(O)C.O1CCCC1.[Ni]>[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[C:13]1[C:25]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]([NH2:26])[C:17]=2[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 2

HCID 136404568HCID 136404568, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68792857HCID 68792857, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

In a 100 mL autoclave, dissolve 0.9 g of equimolecular mixture of the Z and E isomers of 4-(quinolin-2-yl)-fluoren-9-one oxime, obtained in Stage 3, in a mixture of 40 mL of ethanol and 40 mL of tetrahydrofuran, add a spatula tip of Raney nickel, then submit to an initial hydrogen pressure of 1 bar and heat the autoclave at 60° C. for 2 hours. After cooling, filter the catalyst on Celite and concentrate the filtrate at reduced pressure. After purification by flash chromatography on silica gel (20-40 μm), eluting with a mixture of dichloromethane and methanol (95-05 by volume), we obtain 0.72 g of 4-(quinolin-2-yl)-9H-fluoren-9-(R,S)-yl-amine in the form of a white meringue with the following characteristics:

Workup

  1. temperatureAfter cooling
  2. filtrationfilter the catalyst on Celite
  3. concentrationconcentrate the filtrate at reduced pressure
  4. customAfter purification by flash chromatography on silica gel (20-40 μm)
  5. washeluting with a mixture of dichloromethane and methanol (95-05 by volume), we

Sources & evidence

ORD record
ord-e9c4e775a6534c32b2706d452ce5c6b1
Source dataset
uspto-grants-2012_04
Patent number
US08163750B2

Reaction notes

Loading…