HCID 70980137, compound → [3,3'-Bipyridine]-6-carboxylic acid

HRID 1409354Notes

Reaction equation

HRID 1409354 reaction equation
[N:1]1[C:6]([C:7]([O:9]C(C)(C)C)=[O:8])=[CH:5][CH:4]=[C:3]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:2]=1>Cl.O1CCOCC1>[N:1]1[C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=[C:3]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:2]=1

Participants

4

Reactant 1

HCID 70980137HCID 70980137, compound

Product 1

HCID 46316070[3,3'-Bipyridine]-6-carboxylic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 3,3′-bipyridine-6-carboxylate (3.2 g, 12.5 mmol) in 4 M HCl in dioxane (100 ml) was stirred at 110° C. overnight. The reaction mixture was evaporated completely under reduced pressure and triturated twice from diethyl ether. Yield 3.2 g. 1H-NMR (400 MHz; D2O): δ 8.23-8.27 (m, 1H), 8.50 (d, 1H), 8.84 (d, 1H), 8.93 (d, 1H), 8.98 (d, 1H), 9.16 (s, 1H), 9.26 (s, 1H).

Workup

  1. customThe reaction mixture was evaporated completely under reduced pressure
  2. customtriturated twice from diethyl ether

Sources & evidence

ORD record
ord-c179c5e4a58c4daabb6429b43df04e21
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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