Nicotinic acid, hydrazide

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Weigh the methyl 3-picolinate (2.74g, 20mmol)And anhydrous ethanol (15 mL) was added to a 50 mL round bottom flask, Stir at room temperature until the solid completely dissolves, Slowly dropping 30mmol of 80percent hydrazine hydrate, A large number of needle-like white solids appeared immediately, Continue stirring at room temperature for 3h, filter, rinse with a small amount of ethanol, Get 2.56g white needle crystals, Yield 93.2percenta. PREPARATION OF NICOTINOHYDRAZIDE [00473] To a solution of methyl nicotinate (0.73 mmol) in 0.3 mL of ethanol was added hydrazine hydrate (0.35 mL, 7.29 mmol). This reaction mixture was heated in a microwave reactor for 5 min at 150 °C. The reaction was allowed to cool to room temperature and diluted with 10 mL of MeOH, then concentrated. The residue was purified by column chromatography with MeOH/CHA mixture of nicotinic acid (3 g, 24 mmol), MeOH (60 mL) and HSpecific steps for synthesizing nicotinic acid hydrazide:4 g of methyl nicotinate and 25 mL of hydrazine hydrate were weighed and dissolved in 5 mL of anhydrous methanol. Stir at room temperature for 12 hours. Thin layerAfter the chromatographic reaction is completed, the solvent is removed by rotary distillation under reduced pressure.The residue was recrystallized from dry ethyl acetate to afford white crystal. The yield was 67percent.Hydrazine hydrate (25mL) was added to a solution of 2 (4g, 9.2mmol) in methanol (5mL) at the room temperature. The solution was stirred overnight at room temperature. The solvent was evaporated and the crude product was recrystallized from ethanol to give the white solid 3. Yield: 2.69g (67.3percent). IR (KBr, v in cmGeneral procedure: A solution of the appropriate ethyl or methyl esters 21a-d (1.0 mmol) in methanol (5 mL) was prepared in a 10 mL CEM microwave vessel. Hydrazine hydrate 50percent (5.0 mmol) was added, the vessel was capped and placed in a microwave reactor and the reaction carried out with the following method in dynamic mode: 140° C, 60 min, 100 W, with high stirring. After completion the reaction mixture was transferred to a round bottom flask and the solvent evaporated under reduced pressure. The crude product was transferred to an Erlenmeyer flask and suspended in dichloromethane, heated at 50° C for 5 min, rapidly vacuum filtered and washed with the same solvent, to obtain the pure product (yield 80-90percent). When the product was found to be still not pure, the purification procedure was repeated.Nicotinic acid ethyl ester 4 (1.5g, 10mmol) was dissolved in15mL of ethanol, then under ice-cooling was slowly added dropwise with hydrazine hydrate (2g, 40mmol), after the addition was complete, it was stirred at room temperature for 15min, then heated under reflux for 10h. After completion of the reaction, ethanol was removed by rotary evaporation, poured into water, extracted with ethyl acetate, the organic phase was dried andconcentrated to give the desired product 5 (1.1g, 78percent), without purification into the next step.General procedure: An ethanol (300 ml) suspension of salicylic acid(13.8 g; 0.1 mol) and strongly acidic ion-exchange resin, Amberlyst-15 (5 g) were stirred with refluxing for three days.Insoluble catalyst was separated by filtration, and washed withethanol (3 20 ml). Combined ethanol filtrates were mixed with hydrazine hydrate (20 ml; 20.5 g; 0.4 mol) and refluxed with slowsolvent distillation using the modified Hickman still apparatus(Scheme 3). After 3 h of refluxing, the volume of the reaction mixturewas reduced to about 50 ml and white precipitate started toform. The white suspension was cooled to room temperature andthen left at 5 C for 1 h. Insoluble product was separated by filtration, washed with ice cold ethanol, and dried on air to give pureproduct (13.2 g; 87percent).General procedure: The obtained compounds II was dissolved with ethanol (90 mL) and hydrazine hydrate (85percent, 30 mL), then the mixture was heated to reflux for 6 h. After the reaction was completed, ethanol and the excess of hydrazine hydrate were distilled out under a reduced pressure, and a white product was left. The crude product was recrystallized from ethanol to afford white crystals III.

An Impurity of Isoniazid (I821450), potent antitubercular agent against M. tuberculosis.

Molecular Weight:137.14
XLogP3:-0.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:137.058911855
Monoisotopic Mass:137.058911855
Topological Polar Surface Area:68
Heavy Atom Count:10
Complexity:126
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes