Ethanol → Ethyl 5,6-Dichloronicotinate

HRID 1850177Notes

Reaction equation

HRID 1850177 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].Cl[Si](C)(C)C.[CH3:17][CH2:18]O>>[Cl:1][C:2]1[C:3]([Cl:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([O:9][CH2:17][CH3:18])=[O:8]

Participants

4

Reactant 3

HCID 702EthanolHCID 6397ChlorotrimethylsilaneHCID 2479875,6-Dichloronicotinic acid

Product 1

HCID 16762519Ethyl 5,6-Dichloronicotinate

Procedure

To a solution of 5,6-dichloronicotinic acid (20.01 g, 104 mmol) in EtOH (500 mL) at 20° C. was added chlorotrimethylsilane (132 mL, 1042 mmol). The reaction was stirred for 72 hours. The reaction mixture was then concentrated and diluted with EtOAc (500 mL), and washed with saturated NaHCO3 (2×100 mL) and brine (100 mL). The organic was then dried (Na2SO4) and concentrated under reduced pressure to give final crude product (21.25 g). LCMS m/z 220.1 (M+H)+, Rt 0.94 min.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. additiondiluted with EtOAc (500 mL)
  3. washwashed with saturated NaHCO3 (2×100 mL) and brine (100 mL)
  4. dry with materialThe organic was then dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-795d054b462b4807a6db7c5be34627dc
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

Loading…