Hydrochloric Acid → HCID 68140900, compound

HRID 1730276Notes

Reaction equation

HRID 1730276 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][CH:4]([CH2:18][OH:19])[CH2:3]1.Cl>[Zn].O>[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

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 20841815HCID 20841815, compound

Product 1

HCID 68140900HCID 68140900, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

A suspension of 8.13 g. of 6-methyl-8-hydroxymethylergoline and 560 g. of zinc metal dust in 250 ml. of water was cooled to 5° C. in an ice-water bath and stirred. To the cold reaction mixture was added 2500 ml. of concentrated hydrochloric acid dropwise over 6 hours. The acidic aqueous reaction mixture was filtered and the filtrate was made alkaline by the addition of ammonium hydroxide. The aqueous alkaline reaction mixture was extracted with chloroform, and the combined chloroform extracts were washed with water, dried, and the solvent was removed under reduced pressure to afford an oil. The oil was crystallized from methanol,providing 2,3-dihydro-6-methyl-8-hydroxymethylergoline, M.P. 226°-228° C.

Workup

  1. additionA suspension of 8.13 g
  2. customTo the cold reaction mixture
  3. additionwas added 2500 ml
  4. filtrationThe acidic aqueous reaction mixture was filtered
  5. additionby the addition of ammonium hydroxide
  6. customThe aqueous alkaline reaction mixture
  7. extractionwas extracted with chloroform
  8. washthe combined chloroform extracts were washed with water
  9. customdried
  10. customthe solvent was removed under reduced pressure
  11. customto afford an oil
  12. customThe oil was crystallized from methanol,providing 2,3-dihydro-6-methyl-8-hydroxymethylergoline, M.P. 226°-228° C.

Sources & evidence

ORD record
ord-e3d54f37b36f44238cac41fd8ae36c10
Source dataset
uspto-grants-1976_11
Patent number
US03992385

Reaction notes

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