Water → 2-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-N'-hydroxyacetimidamide

HRID 455132Notes

Reaction equation

HRID 455132 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]3[C:16]=2[CH2:17][C:18]#[N:19])=[CH:4][CH:3]=1.[NH2:20][OH:21].Cl.C([O-])([O-])=O.[K+].[K+].O>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]3[C:16]=2[CH2:17][C:18](=[N:20][OH:21])[NH2:19])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 872822-(4-Chlorophenyl)imidazo(1,2-a)pyridine-3-acetonitrileHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 866551272-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-N'-hydroxyacetimidamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)acetonitrile (0.13 mol, 34.0 g) in absolute EtOH (300 mL) was added NH2OH.HCl (0.32 mol, 22.1 g) and K2CO3 (0.32 mol, 44.1 g), respectively. The mixture was stirred at r.t. overnight, filtrated, and washed with EtOH for 3 times. The EtOH-filtrate was concertrated to small volume, and the precipitation was collected by filtration, to give one partial products. The solid was dispersed into water, sonicated for 10 mins, filtrated, washed with water, and dried in vacuo, to give another partial products. Combined two portions products added up to 25.0 g (65.4%). m/e+=301 (M+H+).

Workup

  1. filtrationfiltrated
  2. washwashed with EtOH for 3 times
  3. customthe precipitation
  4. filtrationwas collected by filtration
  5. customto give one partial products
  6. customsonicated for 10 mins
  7. filtrationfiltrated
  8. washwashed with water
  9. customdried in vacuo
  10. customto give another partial products
  11. additionadded up to 25.0 g (65.4%)

Sources & evidence

ORD record
ord-203af166414a43e1b731287c43365ba9
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

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