HCID 53679748, compound → HCID 54096681, compound

HRID 1720316Notes

Reaction equation

HRID 1720316 reaction equation
[CH:1]([O:4][C:5]([C:7]1[N:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[C:19]=1[CH2:20][O:21][CH3:22])=[CH:16][C:15]([C:23]#[C:24][C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)=[CH:14][CH:13]=3)=[O:6])([CH3:3])[CH3:2]>C(O)C.[Ni]>[CH:1]([O:4][C:5]([C:7]1[N:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[C:19]=1[CH2:20][O:21][CH3:22])=[CH:16][C:15]([CH2:23][CH2:24][C:25]1[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=1)=[CH:14][CH:13]=3)=[O:6])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 53679748HCID 53679748, compound

Product 1

HCID 54096681HCID 54096681, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

100 mg of 6-(4-chlorophenylethinyl)-4-methoxymethyl-β-carboline-3-carboxylic acid isopropyl ester is hydrogenated for 1 hour in 20 ml of ethanol with 1 spatula-tip full of Raney nickel (decanted twice with ethanol) at room temperature and hydrogen standard pressure. After filtering off from the catalyst on silica gel it is concentrated by evaporation and the residue is recrystallized from ethyl acetate/hexane. It yields 59 mg (59% of theory) of 6-(4-chlorophenylethyl)-4-methoxymethyl-β-carboline-3-carboxylic acid isopropyl ester, melting point 182°-184° C.

Workup

  1. custom(decanted twice with ethanol) at room temperature
  2. filtrationAfter filtering off from the catalyst on silica gel it
  3. concentrationis concentrated by evaporation
  4. customthe residue is recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-aefa95fd6a004ebc8ad2b240c4b8c07d
Source dataset
uspto-grants-1996_04
Patent number
US05506234

Reaction notes

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