Hydroxyamine hydrochloride → HCID 21156278, compound

HRID 1904589Notes

Reaction equation

HRID 1904589 reaction equation
[O:1]=[C:2]([C@@H:6]1[CH2:20][C@H:19]2[C@@H:9]([CH2:10][C:11]3[C:21]4[C:14](=[CH:15][CH:16]=[CH:17][C:18]2=4)[NH:13][CH:12]=3)[N:8]([CH3:22])[CH2:7]1)[CH2:3][CH:4]=O.Cl.[NH2:24]O>C(O)(=O)C>[CH3:22][N:8]1[C@H:9]2[C@@H:19]([C:18]3[CH:17]=[CH:16][CH:15]=[C:14]4[C:21]=3[C:11]([CH2:10]2)=[CH:12][NH:13]4)[CH2:20][C@@H:6]([C:2]2[O:1][N:24]=[CH:4][CH:3]=2)[CH2:7]1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 86743140HCID 86743140, compound

Product 1

HCID 21156278HCID 21156278, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 5 g (0.017 mole) of 3-oxo-3-(6-methylergolin-8β-yl)-propionaldehyde in 100 ml of glacial acetic acid and 5 g of hydroxylamine hydrochloride was stirred for 20 hours at room temperature and then poured in ice-cold water. After basification with ammonium hydroxide, the solid which separated was filtered and dissolved in ethyl acetate. The organic solution was washed with brine, dried and the solvent was removed, and the residue was crystallized twice from acetone affording the title compound, 1.8 g; m.p. 132°-134° C.

Workup

  1. additionpoured in ice-cold water
  2. customAfter basification with ammonium hydroxide, the solid which separated
  3. filtrationwas filtered
  4. dissolutiondissolved in ethyl acetate
  5. washThe organic solution was washed with brine
  6. customdried
  7. customthe solvent was removed
  8. customthe residue was crystallized twice from acetone affording the title compound, 1.8 g

Sources & evidence

ORD record
ord-7ab31ea263304d1dbb5db8ed31e34203
Source dataset
uspto-grants-1989_06
Patent number
US04839363

Reaction notes

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