Hydroxyamine hydrochloride → HCID 76584761, compound

HRID 911614Notes

Reaction equation

HRID 911614 reaction equation
Cl.[NH2:2][OH:3].C([O-])(O)=O.[Na+].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]=O)=[CH:12][N:11]=1>O.C(O)C>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]=[N:2][OH:3])=[CH:12][N:11]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 117692346-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 76584761HCID 76584761, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Add hydroxylamine hydrochloride (1.494 g, 21.504 mmol) and a solution of NaHCO3 (2.71 g, 32.256 mmol) in water (15 mL) to a solution of 2-bromo-5-formyl-pyridine (2 g, 10.752 mmol, prepared by following the procedure described in J. Org. Chem. 2004, 69, 250-262) in absolute ethanol (100 mL). Stir the mixture at room temperature for 2 h. Concentrate in vacuo and partition the residue between EtOAc and water. Extract the aqueous phase with EtOAc. Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane and hexane/EtOAc (9:1, 4:1) to afford the desired intermediate as a solid (1.362 g, 63%).

Workup

  1. concentrationConcentrate in vacuo
  2. custompartition the residue between EtOAc and water
  3. extractionExtract the aqueous phase with EtOAc
  4. dry with materialDry the combined organic extracts over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify the crude mixture by chromatography on silica gel eluting with hexane and hexane/EtOAc (9:1, 4:1)

Sources & evidence

ORD record
ord-282a14bb17ee46e5864938ad89c67007
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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