Hydroxyamine hydrochloride → N'-Hydroxy-2-(8-bromonaphthalenyl)ethanimidamide

HRID 330511Notes

Reaction equation

HRID 330511 reaction equation
C[O-].[Na+].Cl.[NH2:5][OH:6].[Br:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[C:16]([CH2:18][C:19]#[N:20])=[CH:15][CH:14]=[CH:13]2>CO>[OH:6][N:5]=[C:19]([NH2:20])[CH2:18][C:16]1[C:17]2[C:12](=[CH:11][CH:10]=[CH:9][C:8]=2[Br:7])[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 703577032-(8-Bromonaphthalen-1-yl)acetonitrile

Product 1

HCID 54554816N'-Hydroxy-2-(8-bromonaphthalenyl)ethanimidamideYield 62.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of NaOMe (25 wt % in MeOH, 1.6 ml, 6.83 mmol), MeOH (3 mL), and hydroxylamine hydrochloride (0.47 g, 6.83 mmol) was heated for 30 minutes. 8-Bromo-2-naphthalenylacetonitrile (1.12 g, 4.55 mmol) and MeOH (5 mL) were added and heating was continued for 24 hours. The mixture was concentrated, and suspended in H2O (40 mL) and ether (2 mL). The off-white solid was collected by filtration and triturated with ether to give the title compound (790 mg, 62%), m.p. 123°-125° C.

Workup

  1. temperaturewas heated for 30 minutes
  2. temperatureheating
  3. concentrationThe mixture was concentrated
  4. filtrationThe off-white solid was collected by filtration
  5. customtriturated with ether

Sources & evidence

ORD record
ord-e24a25eaa52f48dfa8a5731afc8f16f9
Source dataset
uspto-grants-1990_01
Patent number
US04897405

Reaction notes

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