Pyridine → N-(4-(2-benzoylhydrazinecarbonyl)pyridin-2-yl)benzamide

HRID 714286Notes

Reaction equation

HRID 714286 reaction equation
[C:1]([NH:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][N:18]=1)[C:13]([OH:15])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[C:25]([NH:33][NH2:34])(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.N1C=CC=CC=1>ClCCl.CN(C)C=O.C(OCC)(=O)C>[C:25]([NH:33][NH:34][C:13]([C:12]1[CH:16]=[CH:17][N:18]=[C:10]([NH:9][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:11]=1)=[O:15])(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 11955BenzoylhydrazineHCID 65578Oxalyl chlorideHCID 643938512-Benzamidoisonicotinic acid

Product 1

HCID 67153859N-(4-(2-benzoylhydrazinecarbonyl)pyridin-2-yl)benzamideYield 67.7%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-benzamidoisonicotinic acid (0.30 g, 1.23 mmol) and N,N-dimethylformamide (0.1 mL) in dichloromethane (5 mL) was added oxalyl chloride (0.13 mL, 1.48 mmol) at ambient temperature. The reaction mixture was stirred for 1 hour and concentrated in vacuo. The residue was dissolved in N,N-dimethylformamide (2 mL) and added to a solution of benzohydrazide (0.20 g, 1.48 mmol) and pyridine (0.3 mL, 3.70 mmol) in N,N-dimethylformamide (1 mL) at 0° C. The reaction mixture was warmed to ambient temperature, stirred for 3 hours, diluted with ethyl acetate (30 mL), and washed with water (25 mL) and brine (25 mL). The organic solution was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was recrystallized from ethyl acetate to give N-(4-(2-benzoylhydrazinecarbonyl)pyridin-2-yl)benzamide (0.30 g, 67%): 1H NMR (300 MHz, DMSO-d6) δ 11.01 (s, 1H), 10.80 (s, 1H), 10.59 (s, 1H), 8.61 (s, 1H), 8.02-7.88 (m, 5H), 7.65-7.49 (m, 7H); MS (ES+) m/z 361.4 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in N,N-dimethylformamide (2 mL)
  3. stirringstirred for 3 hours
  4. washwashed with water (25 mL) and brine (25 mL)
  5. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-6125c23d965247a8aa2076fe39cd2146
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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