Pyridine → HCID 73455879, compound

HRID 1635995Notes

Reaction equation

HRID 1635995 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[Cl:28])[C:5]([NH:7][C:8]1[CH:9]=[N:10][C:11]([O:14][C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[CH2:17][CH2:18][C:19]3=O)=[CH:12][CH:13]=1)=[O:6].[Cl-].[OH:30][NH3+:31].N1C=CC=CC=1>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[Cl:28])[C:5]([NH:7][C:8]1[CH:9]=[N:10][C:11]([O:14][C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[CH2:17][CH2:18][C:19]3=[N:31][OH:30])=[CH:12][CH:13]=1)=[O:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 21645Hydroxylamine HClHCID 9909644HCID 9909644, compound

Product 1

HCID 73455879HCID 73455879, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

800 mg of 3,4-dichloro-N1-{6-[(1-oxo-2,3-dihydro-1H-inden-4-yl)oxy]-3-pyridinyl}benzamide obtained in Example 1 and 670 mg of hydroxyammonium chloride (hydroxylamine hydrochloride) were suspended in 40 ml of ethanol and, after adding 5.4 ml of pyridine to the resulting suspension, the mixture was stirred at 60° C. After 30 minutes, the reaction solution was distilled off under reduced pressure. To the resulting residue, 60 ml of ethyl acetate was added and the solution was washed in turn with water and a saturated sodium chloride solution and then dried over anhydrous magnesium sulfate. After ethyl acetate was distilled off, ether was added to the residue and the deposited crystal was isolated by filtration and then washed with ether to obtain the titled compound (430 mg, white powder).

Workup

  1. distillationthe reaction solution was distilled off under reduced pressure
  2. additionTo the resulting residue, 60 ml of ethyl acetate was added
  3. washthe solution was washed in turn with water
  4. dry with materiala saturated sodium chloride solution and then dried over anhydrous magnesium sulfate
  5. distillationAfter ethyl acetate was distilled off
  6. additionether was added to the residue
  7. customthe deposited crystal was isolated by filtration
  8. washwashed with ether

Sources & evidence

ORD record
ord-9597bff40d98439eaec8bd4d0d74c236
Source dataset
uspto-grants-2003_01
Patent number
US06511995B1

Reaction notes

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