Isopropanol → HCID 21836299, compound

HRID 1908788Notes

Reaction equation

HRID 1908788 reaction equation
[Cl:1][C:2]1[C:3]([Cl:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH:12](O)([CH3:14])[CH3:13]>OS(O)(=O)=O>[CH:12]([O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Cl:1])[C:3]([Cl:11])=[N:4][CH:5]=1)([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 3776IsopropanolHCID 2479875,6-Dichloronicotinic acid

Product 1

HCID 21836299HCID 21836299, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5,6-dichloro nicotinic acid (12.2 g, 63.5 mmol) in isopropanol (70 mL), H2SO4 (4 mL) is added dropwise. The mixture is stirred at 80° C. for 16 h before it is cooled to rt and concentrated in vacuo. The residue is dissolved in dioxane (100 mL) and concentrated again. The crude product is purified by CC (heptane:EA 1:3) to give 5,6-dichloro nicotinic acid isopropyl ester (9.29 g) as a pale beige oil; LC-MS: tR=1.33 min, [M+1]+=233.94.

Workup

  1. temperatureis cooled to rt
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue is dissolved in dioxane (100 mL)
  4. concentrationconcentrated again
  5. customThe crude product is purified by CC (heptane:EA 1:3)

Sources & evidence

ORD record
ord-c088a763004845f780e530311b32d078
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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