Quinoline → HCID 86742053, compound

HRID 231708Notes

Reaction equation

HRID 231708 reaction equation
[C:1]([C:3]1[NH:17][C:16]2[C:18]3[C:4]=1[CH2:5][C@@H:6]1[C@@H:11]([C:12]=3[CH:13]=[CH:14][CH:15]=2)[CH2:10][C@H:9]([NH:19][C:20](=[O:26])[N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[CH2:8][N:7]1[CH3:27])#[CH:2].N1C2C(=CC=CC=2)C=CC=1>C(O)C.[Pd]>[CH3:27][N:7]1[C@H:6]2[C@@H:11]([C:12]3[CH:13]=[CH:14][CH:15]=[C:16]4[C:18]=3[C:4]([CH2:5]2)=[C:3]([CH:1]=[CH2:2])[NH:17]4)[CH2:10][C@H:9]([NH:19][C:20](=[O:26])[N:21]([CH2:22][CH3:23])[CH2:24][CH3:25])[CH2:8]1

Participants

5

Reactant 2

HCID 7047QuinolineHCID 13559048HCID 13559048, compound

Product 1

HCID 86742053HCID 86742053, compoundYield 14.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

200 mg of 3-(2-ethynyl-6-methyl-8α-ergolinyl)-1,1-diethylurea is hydrogenated at room temperature and under normal pressure in 35 ml of ethanol with 200 mg of palladium/calcium carbonate (2%) and 200 mg of quinoline. After the mixture has been filtered off from the catalyst, it is evaporated. The residue is chromatographed over silica gel with methylene chloride/ethanol 6:1, thus obtaining 30 mg of 3-(6-methyl-2-vinyl-8α-ergolinyl)-1,1-diethylurea after recrystallization from ethanol/hexane, mp 145°-150° C.;

Workup

  1. filtrationAfter the mixture has been filtered off from the catalyst, it
  2. customis evaporated
  3. customThe residue is chromatographed over silica gel with methylene chloride/ethanol 6:1

Sources & evidence

ORD record
ord-6ac61faf08c1488ea3cb25522f9ced96
Source dataset
uspto-grants-1989_07
Patent number
US04847262

Reaction notes

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