Sodium Hydroxide → HCID 53772763, compound

HRID 330523Notes

Reaction equation

HRID 330523 reaction equation
Cl.[NH2:2][OH:3].[OH-].[Na+].[Br:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[C:14]2[CH2:17][C:18]#[N:19])=[CH:9][CH:8]=1>CS(C)=O.O>[OH:3][N:2]=[C:18]([NH2:19])[CH2:17][C:14]1[C:15]2[C:10](=[CH:9][CH:8]=[C:7]([Br:6])[CH:16]=2)[CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 70357773HCID 70357773, compound

Product 1

HCID 53772763HCID 53772763, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Hydroxylamine hydrochloride (1.14 g, 16.5 mmol) was dissolved in aqueous sodium hydroxide (1N, 16.5 mL, 16.5 mmol) and the solution diluted with DMSO (50 mL). 7-Bromo-2-naphthalenylacetonitrile (1.35 g, 5.5 mmol) was added in one portion and the resulting mixture heated to 60° C. After a total of 18 hours, the mixture was cooled to room temperature and diluted with water (100 mL) to give a precipitate. The precipitate was collected by filtration, washed with water, and dried in vacuo to give a tan solid (1.24 g, 81%) which was of sufficient purity for use in the subsequent reaction.

Workup

  1. temperatureAfter a total of 18 hours, the mixture was cooled to room temperature
  2. customto give a precipitate
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-47a23d3cc2e744aaadd2f510a5055a3d
Source dataset
uspto-grants-1990_01
Patent number
US04897405

Reaction notes

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