Hydroxyamine hydrochloride → HCID 178464427, compound

HRID 537634Notes

Reaction equation

HRID 537634 reaction equation
[CH2:1]([N:3]([CH2:22][CH2:23][OH:24])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[O:20])[C:12](=O)[CH:11]=2)=[CH:6][CH:5]=1)[CH3:2].Cl.[NH2:26][OH:27]>C(O)C>[CH2:1]([N:3]([CH2:22][CH2:23][OH:24])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[O:20])[C:12](=[N:26][OH:27])[CH:11]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 498449594-(4-(Ethyl(2-hydroxyethyl)amino)phenyl)naphthalene-1,2-dione

Product 1

HCID 178464427HCID 178464427, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 4-(4-(ethyl(2-hydroxyethyl)amino)phenyl)naphthalene-1,2-dione (8.5 g, 26.48 mmol) in absolute ethanol (150 ml) was treated in one portion with hydroxylamine hydrochloride (3.68 g, 52.96 mmol) recrystallised from 75:25 EtOH:H2O and stirred at RT for 2 hrs. The mixture was then evaporated in vacuo and the residue suspended in H2O (500 ml). The aqueous phase was then basified to pH 10 with ammonium hydroxide solution and extracted into EtOAc (×4). The combined organics were then dried (Na2SO4) and evaporated in vacuo to afford the product, 4-(4-(ethyl(2-hydroxyethyl)amino)phenyl)-2-(hydroxyimino)naphthalen-1(2H)-one, as a dark red solid (9.1 g, 100%). Analysis of the product by 1H NMR gave a spectrum consistent with the structure.

Workup

  1. customrecrystallised from 75:25 EtOH
  2. customThe mixture was then evaporated in vacuo
  3. extractionextracted into EtOAc (×4)
  4. dry with materialThe combined organics were then dried (Na2SO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-7703511bee304673bb000e11d7eb6f9c
Source dataset
uspto-grants-2014_10
Patent number
US08865029B2

Reaction notes

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