Ethylene Glycol → HCID 13806529, compound

HRID 2165257Notes

Reaction equation

HRID 2165257 reaction equation
[CH:1]([N:4]1[C:18]2[C:19]3[C:6]([CH2:7][C@@H:8]4[C@@H:13]([C:14]=3[CH:15]=[CH:16][CH:17]=2)[CH2:12][C@@H:11]([C:20]([O:22]C)=[O:21])[CH2:10][N:9]4C#N)=[CH:5]1)([CH3:3])[CH3:2].[OH-].[Na+].C(O)CO.O>C(O)(=O)C>[CH:1]([N:4]1[C:18]2[C:19]3[C:6]([CH2:7][C@@H:8]4[C@@H:13]([C:14]=3[CH:15]=[CH:16][CH:17]=2)[CH2:12][C@@H:11]([C:20]([OH:22])=[O:21])[CH2:10][NH:9]4)=[CH:5]1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 14798Sodium HydroxideHCID 13806525HCID 13806525, compound

Product 1

HCID 13806529HCID 13806529, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A reaction mixture was prepared by combining 25 g of methyl 1-isopropyl-6-cyanoergoline-8β-carboxylate. 8.89 NaOH pellets and 250 ml of ethylene glycol. The reaction mixture was heated in the range 130°-40° C. for about 3 hours. 750 ml of water were added. The pH of the resulting solution was adjusted to about 5 with glacial acetic acid (30 mls.). Crystals began to form and the solution was chilled overnight. The crystals were separated by filtration and the filter cake washed with water; yield (after drying)=19.6 g of 1-isopropylergoline-8β-carboxylic acid, (97.3% pure by HPLC).

Workup

  1. customA reaction mixture was prepared
  2. temperatureThe reaction mixture was heated in the range 130°-40° C. for about 3 hours
  3. customto form
  4. temperaturethe solution was chilled overnight
  5. customThe crystals were separated by filtration
  6. washthe filter cake washed with water
  7. customyield
  8. dry with material(after drying)=19.6 g of 1-isopropylergoline-8β-carboxylic acid, (97.3% pure by HPLC)

Sources & evidence

ORD record
ord-e17d0fe431f14c6f80b23e7d5d76c619
Source dataset
uspto-grants-1990_07
Patent number
US04939258

Reaction notes

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