Pyridine → HCID 68141288, compound

HRID 1730277Notes

Reaction equation

HRID 1730277 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[CH:14]([CH2:15]2)[CH2:13][NH:12]4)[CH2:5][CH:4]([CH2:18][OH:19])[CH2:3]1.N1[CH:25]=[CH:24]C=CC=1.[C:26](OC(=O)C)(=[O:28])[CH3:27].[OH-:33].[NH4+]>C(OCC)(=O)C.O>[C:26]([N:12]1[C:11]2[C:17]3[CH:14]([CH2:15][C@@H:16]4[C@@H:6]([C:7]=3[CH:8]=[CH:9][CH:10]=2)[CH2:5][CH:4]([CH2:18][O:19][C:24](=[O:33])[CH3:25])[CH2:3][N:2]4[CH3:1])[CH2:13]1)(=[O:28])[CH3:27]

Participants

7

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 14923Ammonium HydroxideHCID 68140900HCID 68140900, compound

Product 1

HCID 68141288HCID 68141288, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution 1 g. of 2,3-dihydro-6-methyl-8-hydroxymethylergoline in 50 ml. of pyridine containing 25 ml. of acetic anhydride was stirred at 25° C. for 15 hours. The reaction mixture was added to 100 ml. of water, and the pH of the aqueous layer was adjusted to 10 by the addition of ammonium hydroxide. The aqueous alkaline reaction mixture was extractedwith ethyl acetate, and the organic extracts were combined, washed with water, dried, and the solvent was removed therefrom under reduced pressureto provide an oil. The oil was crystallized from methanol, affording 1-acetyl-2,3-dihydro-6-methyl-8-acetoxymethyl-ergoline, M.P. 172°-177° C.

Workup

  1. additionThe reaction mixture was added to 100 ml
  2. customThe aqueous alkaline reaction mixture
  3. washwashed with water
  4. customdried
  5. customthe solvent was removed
  6. customprovide an oil
  7. customThe oil was crystallized from methanol

Sources & evidence

ORD record
ord-4bb3b51ca5174dc3bd6b14f4a197becc
Source dataset
uspto-grants-1976_11
Patent number
US03992385

Reaction notes

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