Methane → 6-Methyl-8-(2-methoxy-5-pyridylamino)ergoline

HRID 1415295Notes

Reaction equation

HRID 1415295 reaction equation
[CH3:1][N:2]1[C@H:16]2[C@@H:6]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:17]=3[C:14]([CH2:15]2)=[CH:13][NH:12]4)[CH2:5][C:4](=O)[CH2:3]1.C.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][N:23]=1.[H][H]>C(O)(=O)C.[Pd]>[CH3:1][N:2]1[C@H:16]2[C@@H:6]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:17]=3[C:14]([CH2:15]2)=[CH:13][NH:12]4)[CH2:5][CH:4]([NH:28][C:25]2[CH:26]=[CH:27][C:22]([O:21][CH3:20])=[N:23][CH:24]=2)[CH2:3]1

Participants

7

Reactant 4

HCID 297MethaneHCID 811216-Methoxy-3-pyridinylamineHCID 116228296-Methyl-8-oxo-ergolineHCID 178418361HCID 178418361, compound

Product 1

HCID 681219156-Methyl-8-(2-methoxy-5-pyridylamino)ergoline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent2×

Procedure

A solution of 35.6 g of 6-methyl-8-oxo-ergoline in 1.4 liters of glacial acetic acid is slowly added dropwise to 35 g of 10% palladium on active charcoal and 18.6 g of 2-methoxy-5-aminopyridine in 400 cc of glacial acetic acid with simultaneous hydrogenation under normal conditions. The addition is effected within about 7 hours. After the hydrogen take up is complete, the catalyst is filtered off, the filtrate is concentrated in a vacuum and the resulting residue is taken up in methylene chloride (+15% of isopropanol) and washed with ice-cooled ammonia and water. The residue obtained after drying the combined organic phases and concentrating by evaporation, is purified and separated into the isomers by chromatography on an 80-fold quantity of silica gel with methylene chloride and the addition of increasing amounts of methanol.

Workup

  1. additionThe addition
  2. filtrationthe catalyst is filtered off
  3. concentrationthe filtrate is concentrated in a vacuum
  4. washwashed with ice-
  5. temperaturecooled ammonia and water
  6. customThe residue obtained
  7. customafter drying the combined organic phases
  8. concentrationconcentrating by evaporation
  9. customis purified
  10. customseparated into the isomers by chromatography on an 80-fold quantity of silica gel with methylene chloride
  11. additionthe addition of increasing amounts of methanol

Sources & evidence

ORD record
ord-fd75daa43f7e40d387338fbcbe503743
Source dataset
uspto-grants-1977_01
Patent number
US04004011

Reaction notes

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