Benzyl 6-aminonicotinate synthesis
- Product Name:Benzyl 6-aminonicotinate
- CAS Number:935687-49-3
- Molecular formula:C13H12N2O2
- Molecular Weight:228.25
3167-49-5
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$8.00/5g
100-39-0
425 suppliers
$10.00/10g
935687-49-3
52 suppliers
$62.00/250mg
Yield:935687-49-3 65%
Reaction Conditions:
Stage #1: 6-aminonicotinic acidwith potassium carbonate;N,N-dimethyl-formamide for 0.166667 h;
Stage #2: benzyl bromide at 20;
Steps:
To a stirred suspension of 6-aminonicotinic acid (100 g, 0.72 mol; Aldrich Chemical Company, Inc., Milwaukee, Wl) in N,N-dimethylformamide (700 ml_) with brisk mechanical stirring was added potassium carbonate (150 g, 1.08 mol) and the reaction was stirred for 10 min before the portionwise addition of benzyl bromide (95 ml_, 0.80 mol). The reaction was stirred at room temperature overnight, then the solids were filtered off and washed thoroughly with ethyl acetate, and the solvent was removed under vacuum. The filter cake was dissolved in water and extracted with ethyl acetate. The residue after evaporation of N,N-dimethylformamide was combined with the ethyl acetate extracts (total volume 2 L of ethyl acetate) and the combined organic extracts washed with brine (5 * 500 ml_), dried (MgSO4) and the solvent removed under reduced pressure. The crude product was refluxed with 1 :1 diethyl etherhexane for 30 min then the solids filtered off (warm), washed with diethyl etherhexane (1 :1 ), and dried. This solid was precipitated from hot toluene (hot filtration required to remove dibenzylated material) and dried to afford (l-28a) (107.2 g, 65%) as an off-white solid; 1H NMR (DMSO-de): δ 8.50 (1 H), 7.82 (1 H), 7.34-7.29 (5 H), 6.84 (2 H), 6.43 (1 H), 5.23 (2 H); m/z 229.4 (M+H)+.
References:
WO2010/29461,2010,A1 Location in patent:Page/Page column 65-66
3167-49-5
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$8.00/5g
100-51-6
1381 suppliers
$5.00/100g
935687-49-3
52 suppliers
$62.00/250mg
1072-97-5
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124-38-9
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100-39-0
425 suppliers
$10.00/10g
935687-49-3
52 suppliers
$62.00/250mg