Hydroxyamine hydrochloride → HCID 54444278, compound

HRID 330274Notes

Reaction equation

HRID 330274 reaction equation
[CH3:1][O-:2].[Na+].[ClH:4].[NH2:5][OH:6].Cl[C:8]1[C:16]2OC=[C:13]([CH2:17][C:18]#[N:19])[C:12]=2[CH:11]=[CH:10][CH:9]=1>CO>[OH:6][N:5]=[C:18]([NH2:19])[CH2:17][C:13]1[C:12]2[CH:16]=[CH:8][CH:9]=[C:10]([Cl:4])[C:11]=2[O:2][CH:1]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 14819342HCID 14819342, compound

Product 1

HCID 54444278HCID 54444278, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A stirred mixture of NaOMe (25 wt % in MeOH, 11.3 mL, 0.0493 mol), MeOH (40 mL), and hydroxylamine hydrochloride (3.4 g, 0.0493 mol) was heated under reflux for 1 hour. 7-Chloro-3-benzofuranylacetonitrile (6.3 g, 0.0329 mol) and MeOH (15 mL) were added and heating was continued for 2 days. The mixture was concentrated, suspended in H2O, and filtered. The solid was triturated with ether to give the product (5.4 g, 73%) as a tan solid, m.p. 142°-145° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. temperatureheating
  4. concentrationThe mixture was concentrated
  5. filtrationfiltered
  6. customThe solid was triturated with ether

Sources & evidence

ORD record
ord-6076322030904576890bf19a81d0c79c
Source dataset
uspto-grants-1990_01
Patent number
US04895860

Reaction notes

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