ChemicalBook CAS DataBase List 2,2'-DIPICOLYLAMINE

2,2'-DIPICOLYLAMINE synthesis

12synthesis methods

Product Name:2,2'-DIPICOLYLAMINE
CAS Number:1539-42-0
Molecular formula:C12H13N3
Molecular Weight:199.25

100-70-9 Synthesis

100-70-9
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1539-42-0
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$16.00/1g

Yield:1539-42-0 99.7%

Reaction Conditions:

with 5%-palladium/activated carbon;hydrogen in ethanol; for 72 h;Molecular sieve;

Steps:

3 Example 3: Preparation of 2,2’-Dipicolylamine (DPA)

To a round bottom flask equipped with a magnetic stir bar was added; 10.1015 g 2-cyanopyridine [96.05 mmol], 0.4966g 5% (wt/wt) Palladium on Carbon and 16.5 mL of anhydrous ethanol stored over 4 A molecular sieves. The reaction mixture was then slowly flushed with 3 L of H2(g) and once flushed, a vacuum was pulled on the reaction mixture before a balloon of hydrogen 1 L was placed on top to incorporate overnight. The reaction vessel was flushed with a balloon of fresh hydrogen every day. Reaction progress was monitored by TLC [Eluent - 20% CH3OH: 80% CH2C12] and visualized with acidic ninhydrin stain. The reaction occurred over 72 hours, after which TLC indicated the consumption of starting material. 1001511 Isolation of 2,2 ‘-Dipicolylamine: The reaction mixture was filtered through a 1 cmthick layer of packed celite by vacuum filtration. The celite was then washed with 50 mL of hotethanol and the collected filtrates were combined and concentrated by rotary evaporation. Theafforded 9.540 g [99.7% isolated] of transparent amber oil was verified by ESI-LCMS [M/Z+1200.1 positive ionization - IVJIZ-1 : 198.95 negative ionization] and 1H NMR.1001521 1HNMR 300 MHz [CD3C1]: 3.97, s,H4; 7.21,t(Jc. 6.9Hz),H2; 7.38, d(Jc. 8.7Hz), H 2; 7.64, td (Jc. 6.9 Hz) H 2; 8.55, d (Jc. 7.2 Hz) H 2.

References:

WO2017/66672,2017,A1 Location in patent:Paragraph 00150; 00151; 00152