ChemicalBook CAS DataBase List 2-Dimethylaminopyridine

2-Dimethylaminopyridine synthesis

9synthesis methods

Product Name:2-Dimethylaminopyridine
CAS Number:5683-33-0
Molecular formula:C7H10N2
Molecular Weight:122.17

504-29-0
556 suppliers
$5.00/5 g

50-00-0 Synthesis

50-00-0
895 suppliers
$10.00/25g

5683-33-0
151 suppliers
$25.60/5g

Yield:5683-33-0 55%

Reaction Conditions:

Stage #1:2-aminopyridine;formaldehyd with sodium cyanoborohydride in water;acetonitrile at 0; for 0.166667 h;
Stage #2: with acetic acid in water;acetonitrile at 20; for 15 h;
Stage #3: with sodium hydroxide in water

Steps:

9.E.1
Dimethyl-pyridin-2-yl-amineTo an ice-cold solution of 2-aminopyridine (5.0 g, 53.12 mmol) in acetonitrile (150.0 mL) was added sequentially water (33.0 mL) followed by formaldehyde (37% aq. solution, 50.0 mL) and sodium cyanoborohydride (10.0 g, 159.13 mmol). The resulting reaction mixture was stirred at O⁰C for 10 min followed by drop wise addition of acetic acid (12.0 mL). The reaction mixture was then allowed to stir at room temperature for 15 h. After the completion of the reaction (TLC monitoring), the solvent was evaporated and the residue was treated with aqueous NaOH (2N, 50.0 ml.) and extrated with hexane (3 x 50 .0 ml_). The combined organics was washed with brine, dried (Na₂SO₄), filtered and concentrated. The residue was purified over silica gel (100-200 M, 2% EtOAc-Hexane) to get the desired compound (3.50 g,55%).¹H-NMR (400 MHz, DMSOd₆): δ 2.99 (s, 6H)₁ 6.52-6.55 (m, 1 H), 6.61 (d, J= 8.80 Hz,1 H), 7.44-7.49 (m, 1 H) and 8.07 (m, 1 H). MS: 123.10 (M+H)⁺.

References:

PROLYSIS LTD. WO2007/148093, 2007, A1 Location in patent:Page/Page column 68-69

FullText