N'-Acetyl-6-chloronicotinohydrazide → 2-Chloro-5-(5-methyl-1,3,4-oxadiazol-2-yl)pyridine

HRID 385937Notes

Reaction equation

HRID 385937 reaction equation
[C:1]([NH:4][NH:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[N:9][CH:8]=1)(=O)[CH3:2]>O1CCCC1.C(OCC)(=O)C>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]2[O:14][C:1]([CH3:2])=[N:4][N:5]=2)=[CH:8][N:9]=1

Participants

4

Reactant 1

HCID 30905803N'-Acetyl-6-chloronicotinohydrazide

Product 1

HCID 126375112-Chloro-5-(5-methyl-1,3,4-oxadiazol-2-yl)pyridine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

N′-Acetyl-6-chloronicotinohydrazide (95 mg, 0.45 mml) and 3,3,3-triethyl-1-(methoxycarbonyl)diazathian-3-ium-1-ide 2,2-dioxide (159 mg, 0.67 mmol) were taken up in tetrahydrofuran (4.5 mL) and heated in a microwave at 120° C. for 30 minutes. The reaction was then diluted with ethyl acetate and washed with saturated aqueous ammonium chloride, water, and brine. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo to afford the title compound.

Workup

  1. washwashed with saturated aqueous ammonium chloride, water, and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6242391d419e4126bb559c3fab22538d
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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