Isonicotinamide synthesis
- Product Name:Isonicotinamide
- CAS Number:1453-82-3
- Molecular formula:C6H6N2O
- Molecular Weight:122.12
55-22-1
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1453-82-3
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Yield:1453-82-3 95%
Reaction Conditions:
Stage #1: pyridine-4-carboxylic acidwith chloroformic acid ethyl ester;triethylamine in tetrahydrofuran at 0; for 0.5 h;
Stage #2: with ammonium chloride in tetrahydrofuran;water at 0; for 0.5 h;
Steps:
4.2.11 4.2. Typical procedure for the primary amidation of 3-phenylpropanoic acid 1a with NH4Cl
General procedure: To a colorless solution of 75mg (0.50mmol) of 3-phenylpropanoic acid 1a in 10mL of THF were added at 0°C 67μL (0.70mmol, 1.4equiv) of ClCO2Et and 209μL (1.5mmol, 3.0equiv) of Et3N.
After stirring for 30min at 0°C, 0.75 ml of a 1.0M aqueous solution of NH4Cl (0.75mmol, 1.5equiv) was added at 0°C to the colorless suspension.
The mixture was stirred for 30min at 0°C and 5mL of H2O was added to the resulted mixture.
The colorless clear solution was extracted with 30mL of EtOAc and the aqueous layer was extracted with 20mL of EtOAc.
The organic layers were combined, washed with 5mL of brine, and dried over anhydrous MgSO4.
The crude product was chromatographed on silica gel with EtOAc to afford 72mg (96% yield) of 3-phenylpropanamide 2a. 4.2.11
Isonicotinamide 2k
58?mg (95%); colorless solid; mp: 151-153?°C; 1H NMR (400?MHz, DMSO-d6): δ 7.73 (br, 1H, NHA), 7.76, 8.72 (d, d, J?=?6.0, 6.0?Hz, 2H, 2H, pyridyl), 8.25 (br, 1H, NHB); 13C NMR (100?MHz, DMSO-d6): δ 121.3, 141.2, 150.1, 166.2; IR (KBr, vmax/cm-1)?=?3334 (CONH), 1684 (CON), 1624 (CON); HRMS (ESI-TOF): Calcd for C6H7N2O (M+H)+: 123.0553, found: 123.0529.
References:
Ezawa, Tetsuya;Kawashima, Yuya;Noguchi, Takuya;Jung, Seunghee;Imai, Nobuyuki [Tetrahedron Asymmetry,2017,vol. 28,# 12,p. 1690 - 1699]
696-54-8
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1453-82-3
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100-48-1
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1453-82-3
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3731-53-1
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$6.00/5g
1453-82-3
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108-89-4
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$14.00/25mL
1453-82-3
379 suppliers
$5.00/250mg