Acetohydrazide → N'-Acetyl-6-chloronicotinohydrazide

HRID 385936Notes

Reaction equation

HRID 385936 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][N:3]=1.[C:11]([NH:14][NH2:15])(=[O:13])[CH3:12]>CN(C)C=O>[C:11]([NH:14][NH:15][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[N:3][CH:4]=1)(=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 14039AcetohydrazideHCID 27821656-Chloronicotinoyl Chloride

Product 1

HCID 30905803N'-Acetyl-6-chloronicotinohydrazide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Chloronicotinoyl chloride (500 mg, 2.84 mmol) and acetohydrazide (232 mg, 3.12 mmol) were added to dimethylformamide (14.2 mL) at 0° C. The mixture was allowed to warm to room temperature and maintained at room temperature overnight. The reaction was then slightly concentrated in vacuo and diluted in acetonitrile. This mixture was directly purified via reverse phase HPLC (10-100% acetonitrile/water+0.05% TFA modifier). Fractions containing the desired product were lyophilized and free based using bicarbonate resin to afford the title compound.

Workup

  1. temperaturemaintained at room temperature overnight
  2. concentrationThe reaction was then slightly concentrated in vacuo
  3. additiondiluted in acetonitrile
  4. customThis mixture was directly purified via reverse phase HPLC (10-100% acetonitrile/water+0.05% TFA modifier)
  5. additionFractions containing the desired product

Sources & evidence

ORD record
ord-5f86d67a01f84b2ca71875405dc532f8
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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