3,5-DICHLOROISONICOTINIC ACID

Intermediate 1 A solution of 3, [5-DICHLOROPYRIDINE] (5. [00G, ] 33. [8MMOL)] in THF [(25ML)] was added to a solution of LDA [generated from nBuLi (2.5M solution in hexanes, 14. [9MI, ] 37. [2MMOL)] and diisopropylamine (4. 10g, 5. [7MOI, ] 40. 6mmol)] in THF [(25MOI)] [AT-78 . ' UNDER] nitrogen, to give a yellow/brown slurry. The reaction was stirred for 30min [AT-78XB0;] then C02 gas was bubbled through to give a clear brown solution that slowly gave a precipitate, warmed to room temperature over 2h, then quenched with water [(20MI)] and partitioned between [ET2O] [(100MOI)] and [1 M NAOH] [(100ML).] The aqueous layer was separated and acidified to pH 1 with concentrated hydrochloric acid and then extracted with 10percent [MEOH] in DCM [(100MIX3).] The combined organic layers were dried [(MGS04)] and the solvent removed under vacuum to give a brown solid that was [RECRYSTALLISED] from ethanol and dried under vacuum to give the title compound as pinkish crystals (2.63g, [41percent). 8H] (DMSO-d6) 8.74 (2H, s).A solution of 3, [5-DICHLOROPYRIDINE (5. 00G, ] 33. [8MMOL)] in THF [(25ML)] was added to a solution of LDA [generated from nBuLi (2.5M solution in hexanes, 14. [9MOI, ] 37. [2MMOL)] and diisopropylamine (4. [1 OU, ] 5. [7MI, ] 40. 6mmol)] in THF [(25ML)] at- [78-UNDER] nitrogen, to give a [YELLOW/BROWN SLURRY.] The reaction was stirred for 30min [AT-78G] then COs gas was bubbled through to give a clear brown solution that slowly gave a precipitate, warmed to RT over 2h, then quenched with water [(20MI)] and partitioned between [ET20] [(100ML)] and [1 M NAOH] [(100MI).] The aqueous layer was separated and acidified to pH 1 with concentrated hydrochloric acid and then extracted with 10percent [MEOH] in DCM [(1 00MIX3).] The combined organic layers were dried [(MGS04)] and the solvent removed under vacuum to give a brown solid that was recrystallised from ethanol and dried under vacuum to give the title compound as pinkish crystals (2.63g, [41percent). 5H] (DMSO-d6) 8.74 (2H, s). 8C (DMSO-d6) 163.5, 147.7, 141.0, 126.7.

Molecular Weight:192.00
XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:190.9540837
Monoisotopic Mass:190.9540837
Topological Polar Surface Area:50.2
Heavy Atom Count:11
Complexity:155
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes