ChemicalBook CAS DataBase List 5-(1-Methylethyl)-2-pyridinamine

5-(1-Methylethyl)-2-pyridinamine synthesis

7synthesis methods

Product Name:5-(1-Methylethyl)-2-pyridinamine
CAS Number:603310-75-4
Molecular formula:C8H12N2
Molecular Weight:136.19

1135437-90-9

603310-75-4

Step B: Synthesis of 5-isopropylpyridin-2-amine as an intermediate; [0209] A mixture of 2-nitro-5-(prop-1-en-2-yl)pyridine (0.104 g, 0.63 mmol) with 10% palladium-carbon catalyst (0.011 g, 10 wt%) in ethanol (10 mL) was subjected to a hydrogen atmosphere and stirred at atmospheric pressure for overnight reaction. Upon completion of the reaction, the catalyst was removed by diatomaceous earth filtration and the filtrate was concentrated under reduced pressure to give 5-isopropylpyridin-2-amine (0.120 g, 139% yield) as an oily product. Its structure was confirmed by 1H NMR (500 MHz, CDCl3): δ 7.68 (d, J = 8.1 Hz, 1H), 7.51 (s, 1H), 7.48 (s, 2H), 7.14 (d, J = 9.1 Hz, 1H), 3.45-3.42 (m, 1H), 1.38 (d, J = 8.6 Hz, 6H); ESI MS m/z 137 [M + H]+.

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603310-75-4
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Yield: 100%

Reaction Conditions:

with hydrogen;palladium 10% on activated carbon in ethanol under 760.051 Torr;

Steps:

39.B
Step B: Synthesis of 5-isopropylpyridin-2-amine as an intermediate; [0209] A mixture of 2-nitro-5-(prop-l-en-2-yl)pyridine (0.104 g, 0.63 mmol) and 10% palladium on carbon (0.011 g, 10% by weight) in ethanol (10 mL) was stirred under hydrogen at atmospheric pressure overnight. The reaction was filtered through diatomaceous earth and concentrated under reduced pressure to afford 5-isopropylpyridin-2-amine (0.120 g, 139%) as an oil: ¹H NMR (500 MHz, CDCl₃) δ 7.68 (d, J= 8.1 Hz, IH), 7.51 (s, IH), 7.48 (s, 2H), 7.14 (d, J= 9.1 Hz, IH), 3.45-3.42 (m, IH), 1.38 (d, J= 8.6 Hz, 6H); ESI MS m/z 137 [M+ H]⁺.

References:

The United States of America, as represented by the Secretary, Department of Health and Human Services;Science Applications International Corporation (SAIC);Albany Molecular Research, Inc. WO2009/42907, 2009, A1 Location in patent:Page/Page column 83

848841-59-8 Synthesis