2-CHLORO-4-ETHOXYNICOTINONITRILE synthesis

6synthesis methods

Product Name:2-CHLORO-4-ETHOXYNICOTINONITRILE
CAS Number:98645-45-5
Molecular formula:C8H7ClN2O
Molecular Weight:182.61

95689-38-6 Synthesis

2-[3-(DIMETHYLAMINO)-1-METHOXY-2-PROPENYLIDENE]MALONONITRILE

95689-38-6
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Propanedinitrile, 2-[3-(dimethylamino)-1-ethoxy-2-propen-1-ylidene]-

98645-41-1
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98645-45-5
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Yield:98645-45-5 98%

Reaction Conditions:

Stage #1: 1,1-dicyano-4-(N,N-dimethylamino)-2-methoxy-1,3-butadiene;1,1-Dicyan-4-(N,N-dimethylamino)-2-ethoxy-1,3-butadienwith hydrogenchloride in methanol at 0;
Stage #2: with potassium carbonate in dichloromethane;water;

Steps:

41.41B

Example 41B; 2-Chloro-3 -cyano-4-ethoxypyridine; :To a slurry of a mixture of 2-(3-dimethylamino-l-ethoxy-allylidene)malononitrile and 2-(3-dimethylamino-l-methoxyallylidene)malono-nitrile (85.0 g, 445 mmol) from step 1, in methanol (1200 mL), HCl gas was introduced gently at 0 ⁰C. The reaction mixture became homogeneous in about 1 hr, and was allowed to stir under constant HCl flow for additional 14.5 hours at 0 ⁰C. N₂ was bubled though the reaction mixture for over night, and all the solvent was removed. The residue solid was re-dissolved in CH₂Cl₂, and washed with water/KaCCVwater. Organic layer was separated and dried over Na₂SO₄. Removal of salt and solvent gave a pure product (113.0 g, 98%). IH NMR (CDC13, 300 MHz): δ = 7.96 ppm (d, J= 6.4 Hz, IH); 6.59 (d, J= 6.4 Hz, IH); 3.30 (s, 6H). MS (ESI, M+l): 181.9.

References:

WO2006/81072,2006,A1 Location in patent:Page/Page column 48