ChemicalBook CAS DataBase List N-Methoxy-N-methylnicotinamide

N-Methoxy-N-methylnicotinamide synthesis

6synthesis methods

Product Name:N-Methoxy-N-methylnicotinamide
CAS Number:95091-91-1
Molecular formula:C8H10N2O2
Molecular Weight:166.18

6638-79-5 Synthesis

6638-79-5
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20260-53-1
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95091-91-1
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$60.00/50mg

Yield: 74%

Reaction Conditions:

with pyridine in dichloromethane at 0 - 20; for 4.25 h;

Steps:

N-Methoxy-N-methyl-nicotinamide. (compound 2, Scheme 1 ); Nicotinoyl chloride hydrochloride (compound 1 ) (10 g, 56 mmol) and 6.28 g of N, O- dimethyl-hydroxylamine.HCI (72.8 mmol) were combined in 200 ml dichloromethane. To this mixture was added 18.14 ml of pyridine (in 15 minutes at O⁰C). The reaction mixture was subsequently stirred for 4 hours at room temperature. The reaction was concentrated in vacuo. The resulting residue was taken up in dichloromethane and H₂O (O⁰C), washed with a 2N NaOH solution followed by brine, dried (Na₂SO₄), filtered and concentrated in vacuo. Purification by flash chromatography (MeOH/triethylamine 97/3) afforded compound 2 as an oil (6.92 g, 74%). ¹H- NMR (200 MHz, CDCI₃) δ 8.96 (d, J = 2 Hz, 1 H), 8.69 (d, J = 5 Hz, 2 Hz, 1 H), 8.04 (dt, J = 8 Hz, 2 Hz, 1 H), 7.41 -7.32 (m, 1 H), 3.56 (s, 3H), 3.40 (s, 3H). (TLC MeOH/triethylamine R_f 0.19).

References:

SOLVAY PHARMACEUTICALS B.V. WO2008/129054, 2008, A2 Location in patent:Page/Page column 28

59-67-6 Synthesis