ChemicalBook CAS DataBase List 2-Amino-5-nitronicotinic acid

2-Amino-5-nitronicotinic acid synthesis

4synthesis methods

Product Name:2-Amino-5-nitronicotinic acid
CAS Number:6760-14-1
Molecular formula:C6H5N3O4
Molecular Weight:183.12

5345-47-1 Synthesis

5345-47-1
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$9.00/1g

6760-14-1
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$56.00/100mg

Yield: 52%

Reaction Conditions:

with sulfuric acid;nitric acid at 0 - 20;

Steps:

15.A
Step A: A solution of 2-aminonicotinic acid (1.01 g, 7.31 mmol) was dissolved in concentrated H₂SO₄ (ca 5 mL) and cooled to 0°C. Fuming nitric acid (0.4 mL, 8.6 mmol) was slowly added, and the reaction mixture was allowed to warm to room temperature. The mixture was then poured into ice water (100 mL). The resulting precipitates were filtered, washed with water (3 X 15 mL) and then Et₂O (3 X 10 mL) to afford 2-amino-5-nitronicotinic acid as a solid (1.06 g, 52% yield).

References:

ARRAY BIOPHARMA INC.;GENENTECH, INC.;AHRENDT, Kateri A.;BUCKMELTER, Alexandre J.;GRINA, Jonas;HANSEN, Joshua D.;LAIRD, Ellen R.;NEWHOUSE, Brad;REN, Li;WENGLOWSKY, Steven Mark;FENG, Bainian;MALESKY, Kim;MATHIEU, Simon;RUDOLPH, Joachim;WEN, Zhaoyang;YOUNG, Wendy B. WO2009/111280, 2009, A1 Location in patent:Page/Page column 60