5,6-Dichloronicotinaldehyde

To a 500 mL round-bottom flask, manganese oxide (43.5 g, 0.50 mol) was added to a solution of 2, 3-dichloro-5-hydroxymethylpyridine (3, 8.10 g, 50.0 mmol, Sigma-Aldrich, St. Louis, Mo.) in anhydrous CHTo a 500 mL round-bottom flask, manganese oxide (43.5 g, 0.50 mol) was added to a solution of 2, 3-dichloro-5-hydroxylmethylpyridine (3, 8.10 g, 50.0 mmol, Sigma-Aldrich, St. Louis, Mo.) in anhydrous CHTo a 500 mL round-bottom flask, manganese oxide (43.5 g, 0.50 mol) was added to a solution of 2, 3-dichloro-5-hydroxylmethylpyridine (3, 8.10 g, 50.0 mmol, Sigma-Aldrich, St. Louis, Mo.) in anhydrous CH2, 3-Dichloro-5-formylpyridine. To a 500 mL round-bottom flask, manganese oxide (43.5 g, 0.50 mol) was added to a solution of 2, 3-dichloro-5-hydroxylmethylpyridine (64, 8.10 g, 50.0 mmol) in anhydrous CHTo a 500 mL round-bottom flask, manganese oxide (43.5 g, 0.50 mol) was added to a solution of 2, 3-dichloro-5-hydroxylmethylpyridine (1, 8.10 g, 50.0 mMol) in To a solution of (5, 6-dichloropyridin-3-yl)methanol (23) (1 g, 5.62 mmol) in CHTo a solution of (5, 6-dichloro-3-pyridinyl)methanol (200 mg) in CHPreparation 2; 5, 6-Dichloro-3-pyridinecarbaldehyde (Used to prepare Example 15) To a solution of (5, 6-dichloro-3-pyridinyl)methanol (200 mg) in DCM, molecular sieves (3A) (55 mg) and 4-methyl-morpholine-N-oxide (198 mg) was added and stirred at room temperature for 10 minutes. Then tetra-n-propylammonium perruthenate (VII) (38 mg) was added and stirred overnight. The reaction mixture was filtered and the solvent was evaporated to dryness under vacuum. The residue obtained was purified by chromatography column on silica gel using a mixture of EtOAc/hexane as eluent to give 44 mg (22percent) of the title compound.A 2M solution of LiAIH4 in THF (1 9.2mL, 38.2gmmol) was added to a solution of 5, 6-dichloro-N-methoxy-N-methylnicotinamide (22g, 76.59mo1) in THE (360mL) at -78°C and stirred for 30 mm at sametemperature. The RM was quenched with sat. Na2SO4 solution and filtered the salts through celite bed, washed with EtOAc. The filtrate was dried (anhydr. Na2SO4), filtered and evaporated the solvent under vacuo to give crude as a thick liquid. The crude was purified by CC (0-5percent EtOAc in PE) to give 12g (75percent) of 5, 6-dichloronicotinaldehyde as liquid.

Molecular Weight:176.00
XLogP3:1.9
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:174.9591691
Monoisotopic Mass:174.9591691
Topological Polar Surface Area:30
Heavy Atom Count:10
Complexity:131
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes