Acetic Acid → HCID 53672638, compound

HRID 1731747Notes

Reaction equation

HRID 1731747 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH3:19])=[CH:15][C:14]([C:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:13][CH:12]=3)=[O:5])[CH3:2].C(O)(=O)C.[H][H]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH3:19])=[CH:15][C:14]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 53633506HCID 53633506, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53672638HCID 53672638, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

260 mg of 6-benzoyl-4-methyl-β-carboline-3-carboxylic acid ethyl ester is hydrogenated in 36 ml of absolute ethanol with 2 ml of glacial acetic acid and 100 mg of palladium black for 2 hours at 10 bar hydrogen pressure at 40°-45° C. After separation of the catalyst, the reaction mixture is evaporated. The residue is chromatographed over silica gel, first with toluene:glacial acetic acid:water=10:10:1 and then with toluene:ethanol:water=80:20:1, thus obtaining 27 mg (11%) of 6-benzyl-4-methyl-β-carboline-3-carboxylic acid ethyl ester.

Workup

  1. customAfter separation of the catalyst
  2. customthe reaction mixture is evaporated
  3. customThe residue is chromatographed over silica gel, first with toluene

Sources & evidence

ORD record
ord-f93b1b935b0246bba2681c8e6f12de0f
Source dataset
uspto-grants-1986_11
Patent number
US04623649

Reaction notes

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