Pyridine → HCID 136389799, compound

HRID 1250908Notes

Reaction equation

HRID 1250908 reaction equation
N1C=CC=CC=1.Cl.[NH2:8][OH:9].[CH3:10][C:11]1[C:15]([C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=O)=[N:14][O:13][N:12]=1>C(OCC)(=O)C>[CH3:10][C:11]1[C:15](/[C:16](/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:8]/[OH:9])=[N:14][O:13][N:12]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 13415356(4-Methyl-1,2,5-oxadiazol-3-yl)phenylmethanone

Product 1

HCID 136389799HCID 136389799, compoundYield 21.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A pyridine (55 ml) solution of hydroxylamine hydrochloride (5.19 g, 73.0 mmol) was added to (3-methyl-1, 2, 5-oxadiazol-4-yl) phenylmethanone (3.43 g, 18.0 mmol) and heated to 70° C. for 21 hours with stirring. After the reacted solution was condensed, the residue was dissolved in ethyl acetate. After washing with diluted hydrochloride and subsequent washing with water, the residue was dried with magnesium carbonate. After removing the solvent and purifying the residue by column chromatography, (Z)-(3-methyl-1, 2, 5-oxadiazol-4-yl) phenylmethanone oxime (2.13 g) and (E)-(3-methyl-1, 2, 5-oxadiazol-4-yl)phenylmethanone oxime (0.79 g) were obtained.

Workup

  1. customcondensed
  2. washAfter washing with diluted hydrochloride
  3. washsubsequent washing with water
  4. dry with materialthe residue was dried with magnesium carbonate
  5. customAfter removing the solvent
  6. custompurifying the residue by column chromatography, (Z)-(3-methyl-1, 2, 5-oxadiazol-4-yl) phenylmethanone oxime (2.13 g)

Sources & evidence

ORD record
ord-287cb0bac04247d6a7e18823a1bbaf29
Source dataset
uspto-grants-2002_01
Patent number
US06340697B1

Reaction notes

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