2,4-DICHLORO-6-METHYLNICOTINALDEHYDE synthesis

5synthesis methods

Product Name:2,4-DICHLORO-6-METHYLNICOTINALDEHYDE
CAS Number:91591-72-9
Molecular formula:C7H5Cl2NO
Molecular Weight:190.03

(2,4-DICHLORO-6-METHYLPYRIDIN-3-YL)METHANOL

374800-25-6
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91591-72-9
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Yield:91591-72-9 85%

Reaction Conditions:

with oxalyl dichloride;dimethyl sulfoxide;triethylamine in dichloromethane at -78 - 20; for 1 h;Product distribution / selectivity;

Steps:

6

Intermediate 6DMSO (20 ml, 282 mmol) was added to a stirred solution of oxalyl chloride (12.1 ml, 140 mmol) in DCM (140 ml) at -78°C. After the addition, Intermediate 5 (9.32 g, 49 mmol) in DCM (35 ml) was then added followed by the addition of Et₃N (79 ml, 568 mmol) whilst maintaining the temperature below -70°C. The reaction mixture was allowed to warm to rt and stirred for 1 hour. The reaction mixture was washed with NaHC0₃(aq) solution and the organic phase was dried and concentrated. The residue was purified by flash column chromatography on silica gel eluting with 10:1 petrol-ethyl acetate to give an off-white solid (7.88 g, 85%). H NMR (400 MHz, chloroform-d) δ ppm 2.60 (s, 3 H), 7.27 (s, 1 H), 10.46 (s, 1 H).

References:

WO2011/141756,2011,A1 Location in patent:Page/Page column 51