Hydrochloric Acid → 5-Chloro-6-isopropoxynicotinic acid

HRID 2065869Notes

Reaction equation

HRID 2065869 reaction equation
[Cl:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH3:12][C:13]([O-:16])(C)[CH3:14].[K+].Cl>C(O)(C)C.O>[Cl:1][C:2]1[C:3]([O:16][CH:13]([CH3:14])[CH3:12])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2479875,6-Dichloronicotinic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 180705825-Chloro-6-isopropoxynicotinic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

5,6-Dichloronicotinic acid (1.95 g, 10 mmol) is added to a solution of KOtBu (2.28 g, 20 mmol) in isopropanol (20 mL). The mixture is heated at 80° C. for 15 h. The mixture is diluted with water (60 mL) and acidified with 1M aq. HCl. The aq. solution is extracted with ether (5×50 mL) and the combined org. extracts are dried (Na2SO4), filtered and evaporated to provide 5-chloro-6-isopropoxy-nicotinic acid; 1H NMR (d6-DMSO) δ 1.38 (d, J=6.2 Hz, 7H), 5.44 (hept, J=6.2 Hz, 1H), 8.18 (d, J=2.1 Hz, 1H), 8.65 (d, J=2.1 Hz, 1H)

Workup

  1. extractionThe aq. solution is extracted with ether (5×50 mL)
  2. dry with materialextracts are dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-6e1caddd7cb64525bafab0cb12168c60
Source dataset
uspto-grants-2012_10
Patent number
US08288554B2

Reaction notes

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