Acetamide, N-methyl-N-2-pyridinyl- synthesis

5synthesis methods

Product Name:Acetamide, N-methyl-N-2-pyridinyl-
CAS Number:61996-35-8
Molecular formula:C8H10N2O
Molecular Weight:150.18

4597-87-9
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108-24-7
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61996-35-8
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$285.00/250mg

Yield:61996-35-8 100%

Reaction Conditions:

at 70; for 4 h;

Steps:

4.1.8. N-Methyl-N-(2-pyridyl)acetamide (8)

A mixture of 2-(methylamino)pyridine (857 mg, 7.92 mmol) and acetic anhydride (4.23 g, 41.4 mmol) was heated at 70 °C for 4 h. After removal of the solvent under reduced pressure, chromatography (AcOEt) of the residue gave 8 as a pale brown oil in quantitative yield. ν_max (KBr) 1663, 1587, 1379 cm^-1; ¹H NMR (300 MHz, CD₂C1₂) δ 8.44 (1H, ddd, J 0.8, 2.0, 4.8 Hz), 7.72 (1H, dd, J 2.0, 7.5 Hz), 7.29 (1H, d, J 8.1 Hz), 7.15 (1H, ddd, J 1.0, 4.8, 7.3 Hz), 3.31 (3H, s), 2.03 (3H, s); ¹³C NMR (75 MHz, CDC1₃, 55 °C) δ 170.7, 156.5, 148.9, 138.0, 121.5, 120.3, 35.4, 23.0; m/z (EI) 150; HRMS (EI): M⁺, found 150.0807. C₈H₁₀N₂O requires 150.0794.

References:

Okamoto, Iwao;Terashima, Masayuki;Masu, Hyuma;Nabeta, Mayumi;Ono, Kaori;Morita, Nobuyoshi;Katagiri, Kosuke;Azumaya, Isao;Tamura, Osamu [Tetrahedron,2011,vol. 67,# 44,p. 8536 - 8543] Location in patent:experimental part

109-04-6 Synthesis