Hydrochloric Acid → HCID 178526249, compound

HRID 2085053Notes

Reaction equation

HRID 2085053 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N+:3]=1[O-:8].Cl.[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16].C([O-])(O)=O.[Na+]>C(O)(CC)(C)C>[OH:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][NH:10][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N+:3]=1[O-:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 754652-Chloropyridine oxideHCID 756345-Aminopentan-1-olHCID 516892Sodium Bicarbonate

Product 1

HCID 178526249HCID 178526249, compound

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent

Procedure

2-(5-hydroxypentylamino)pyridine N-oxide was prepared dissolving 2-chloropyridine N-oxide.HCl (18.07 mmol), 5-amino-1-pentanol (36.14 mmol), and NaHCO3 (90.36 mmol) in tert-amyl alcohol (20 mL), then refluxing overnight under Ar. After cooling, the reaction was filtered and concentrated to a green oil. Purification by silica gel chromatography (eluent: 94:5:1 CH2Cl2, MeOH, NH4OH) yielded a yellow solid (3.07 g). 1H NMR was consistent with the desired product.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction was filtered
  3. concentrationconcentrated to a green oil
  4. customPurification by silica gel chromatography (eluent: 94:5:1 CH2Cl2, MeOH, NH4OH)

Sources & evidence

ORD record
ord-f90bb26962a844d9928290dd14f75262
Source dataset
uspto-grants-2004_04
Patent number
US06720315B2

Reaction notes

Loading…