Methane → HCID 68121461, compound

HRID 1415294Notes

Reaction equation

HRID 1415294 reaction equation
C(O)(=O)/C=C\C(O)=O.[CH3:9][N:10]1[C@H:24]2[C@@H:14]([C:15]3[CH:16]=[CH:17][CH:18]=[C:19]4[C:25]=3[C:22]([CH2:23]2)=[CH:21][NH:20]4)[CH2:13][C:12](=O)[CH2:11]1.[NH2:27][C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1.C.[H][H]>CO.[Pd]>[CH3:9][N:10]1[C@H:24]2[C@@H:14]([C:15]3[CH:16]=[CH:17][CH:18]=[C:19]4[C:25]=3[C:22]([CH2:23]2)=[CH:21][NH:20]4)[CH2:13][CH:12]([NH:27][C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)[CH2:11]1

Participants

7

Reactant 4

HCID 297MethaneHCID 100093-AminopyridineHCID 68121989HCID 68121989, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68121461HCID 68121461, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

17.8 g of 6-methyl-8-oxo-ergoline hydrogen maleate and 23.5 g of 3-aminopyridine in 500 cc of methanol are hydrogenated with the addition of 12 g of 10% palladium on active charcoal under normal conditions. After the hydrogen take up is complete (approx. 120 hours), the catalyst is filtered off, the filtrate is concentrated in a vacuum at a water bath temperature of 60°, and the resulting residue is purified and separated by chromatography on a 30-fold quantity of silica gel with methylene chloride and the addition of increasing amounts of methanol.

Workup

  1. custom(approx. 120 hours)
  2. filtrationthe catalyst is filtered off
  3. concentrationthe filtrate is concentrated in a vacuum at a water bath temperature of 60°
  4. customthe resulting residue is purified
  5. customseparated by chromatography on a 30-fold quantity of silica gel with methylene chloride
  6. additionthe addition of increasing amounts of methanol

Sources & evidence

ORD record
ord-8b7d3d3928974cb6995438e27f423b41
Source dataset
uspto-grants-1977_01
Patent number
US04004011

Reaction notes

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