2-Aminonicotinic acid → 3-Pyridinecarboxylic acid, 2-amino-, 2-[4-(1-methylethyl)benzoyl]hydrazide

HRID 1405679Notes

Reaction equation

HRID 1405679 reaction equation
[CH3:1][CH:2]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([NH:10][NH2:11])=[O:9])=[CH:6][CH:5]=1)[CH3:3].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:36][C:37]1[C:42]([C:43](O)=[O:44])=[CH:41][CH:40]=[CH:39][N:38]=1.C(=O)([O-])O.[Na+]>CN(C=O)C.O>[NH2:36][C:37]1[C:42]([C:43]([NH:11][NH:10][C:8]([C:7]2[CH:12]=[CH:13][C:4]([CH:2]([CH3:1])[CH3:3])=[CH:5][CH:6]=2)=[O:9])=[O:44])=[CH:41][CH:40]=[CH:39][N:38]=1

Participants

8

Reactant 5

HCID 729302-Aminonicotinic acidHCID 757711-HydroxybenzotriazoleHCID 2194004-isopropylbenzohydrazideHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 667485333-Pyridinecarboxylic acid, 2-amino-, 2-[4-(1-methylethyl)benzoyl]hydrazideYield 66.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(1-methylethyl)benzohydrazide (2194 mg), HOBt.H2O (2073 mg), EDCI HCl (2595 mg) and 2-aminopyridine-3-carboxylic acid (1700 mg) in dehydrated DMF (50 mL) was stirred at 60° C. overnight. The reaction mixture was added to a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from a mixture of ethyl acetate and diisopropyl ether to give the title compound (2.4489 g) as a white solid. The mother liquor was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (276.1 mg) as a white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was crystallized from a mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-4ddd632b5aac4c1695a1244d50561f1d
Source dataset
uspto-grants-2014_12
Patent number
US08916551B2

Reaction notes

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