Hydroxylamine → 2',3-Dimethyl-[2,4'-bipyridine]-5-carbaldehyde oxime

HRID 711287Notes

Reaction equation

HRID 711287 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH:15]=O)=[CH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1.[OH:17][NH2:18].CC([O-])=O.[Na+].C(OC(C)C)(=O)C>O.C(O)C>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH:15]=[N:18][OH:17])=[CH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 787HydroxylamineHCID 7915Isopropyl AcetateHCID 517045Sodium AcetateHCID 866797232',3-Dimethyl-[2,4'-bipyridine]-5-carbaldehyde

Product 1

HCID 1363597592',3-Dimethyl-[2,4'-bipyridine]-5-carbaldehyde oxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a 5-L four-necked flask equipped with an overhead stirrer, and a thermocouple was charged with 2′,3-dimethyl-[2,4′-bipyridine]-5-carbaldehyde (34d, 1120 mmol), hydrochloro hydroxyamine (34e, 140.1 g, 2016 mmol), and ethanol (1600 mL). The mixture was stirred at 23° C. for 2 h before the addition of NaOAc (183.8 g, 2240 mmol, 2 eq) and iso-propyl acetate (2 L)/water (2 L). The aqueous layer was back-extracted with iso-propyl acetate (2 L) after the layer separation. The combined organic layers were concentrated to almost dryness to afford the crude 2′,3-dimethyl-[2,4′-bipyridine]-5-carbaldehyde oxime (34f) as a brown oil.

Workup

  1. customTo a 5-L four-necked flask equipped with an overhead stirrer
  2. extractionThe aqueous layer was back-extracted with iso-propyl acetate (2 L)
  3. customafter the layer separation
  4. concentrationThe combined organic layers were concentrated to almost dryness

Sources & evidence

ORD record
ord-e4cb9168f1f24ce5bb3a6e42df288d9d
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

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