Pyridine → HCID 54403492, compound

HRID 1761569Notes

Reaction equation

HRID 1761569 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-9ca05c5704ca4272acebe4f7fae3b719
Source dataset
uspto-grants-1989_05
Patent number
US04826868

Reaction notes

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