Water → HCID 21836299, compound

HRID 1739652Notes

Reaction equation

HRID 1739652 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].O.[CH:13](O)([CH3:15])[CH3:14]>>[Cl:1][C:2]1[C:3]([Cl:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([O:9][CH:13]([CH3:15])[CH3:14])=[O:8]

Participants

4

Reactant 3

HCID 962WaterHCID 3776IsopropanolHCID 2479875,6-Dichloronicotinic acid

Product 1

HCID 21836299HCID 21836299, compound

Procedure

5,6-Dichloronicotinic acid (2.00 g, 10.4 mmol) was dissolved in 50 mL isopropanol to which was added BF3 -diethyl etherate (3.84 mL, 3 eq). The solution was refluxed overnight. When cooled, the solution was poured into 100 mL water and extracted with Et2O (2×100 mL) The organics were collected, washed with water, brine, 1.0 N NaOH, dried over MgSO4, and concentrated to give isopropyl 5,6-dichloronicotinate (0.62 g) as a cream solid.

Workup

  1. additionwas added BF3 -diethyl etherate (3.84 mL, 3 eq)
  2. temperatureThe solution was refluxed overnight
  3. temperatureWhen cooled
  4. extractionextracted with Et2O (2×100 mL) The
  5. customorganics were collected
  6. washwashed with water, brine, 1.0 N NaOH
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4d7145503c0c4dd7a93d3f0f3acb338d
Source dataset
uspto-grants-1999_10
Patent number
US05968875

Reaction notes

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