Pyridine → HCID 54403492, compound

HRID 373491Notes

Reaction equation

HRID 373491 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[N:11]=[C:10]([CH2:21][CH2:22][CH:23]=O)[CH:9]=2)=[CH:4][CH:3]=1.Cl.[NH2:26][OH:27].N1C=CC=CC=1>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[N:11]=[C:10]([CH2:21][CH2:22][CH:23]=[N:26][OH:27])[CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 14497520HCID 14497520, compound

Product 1

HCID 54403492HCID 54403492, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the aldehyde 11 (1.00 g, 2.93 mM) in EtOH (30 ml) was added hydroxylamine hydrochloride (0.31 g, 4.40 mM) and pyridine (0.47 g, 5.87 mM). After stirring overnight at room temperature, the reaction mixture was concentrated in vacuo. The remaining residue was taken up in CH2Cl2, washed with H2O, dried (Na2SO4), filtered, and concentrated in vacuo. Crystallization from Et2O:hexane afforded 26, (0.67 g, 64%) as a white crystalline solid, mp=134°-135° C.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. washwashed with H2O
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customCrystallization from Et2O

Sources & evidence

ORD record
ord-b3734dc2af0c466899102fc5f2ef1271
Source dataset
uspto-grants-1992_11
Patent number
US05164381

Reaction notes

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