Hydroxyamine hydrochloride → HCID 85438995, compound

HRID 236719Notes

Reaction equation

HRID 236719 reaction equation
[C:1]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[N:16]1[C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][C:18]([C:25]([O:27][CH3:28])=[O:26])=[N:17]1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:30][OH:31]>N1C=CC=CC=1>[Cl:15][C:13]1[CH:12]=[CH:11][C:10]([N:16]2[C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][C:18]([C:25]([O:27][CH3:28])=[O:26])=[N:17]2)=[C:9]([C:1](=[N:30][OH:31])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:14]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 12377875HCID 12377875, compound

Product 1

HCID 85438995HCID 85438995, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 11.2 g. (28 mmol) of the final product of Example 3, 5.80 g. (84 mmol) of hydroxylamine hydrochloride and 180 ml. pyridine was heated to reflux for 6.5 hours. After cooling to room temperature, the reaction was concentrated in vacuo to remove the pyridine. The crude product, as isolated, was then chromatographed on silica gel, using 10% EtOAc in benzene as eluent, to give the final product. Recrystallization from EtOH/H2O gave an analytical sample as colorless prisms mp: 177°-179°.

Workup

  1. additionA mixture of 11.2 g
  2. temperatureto reflux for 6.5 hours
  3. concentrationthe reaction was concentrated in vacuo
  4. customto remove the pyridine
  5. customThe crude product, as isolated
  6. customwas then chromatographed on silica gel

Sources & evidence

ORD record
ord-c3513be336b046a9b1cc16203c741a97
Source dataset
uspto-grants-1979_06
Patent number
US04157331

Reaction notes

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