Ethanol → Ethyl 2-chloro-6-methylnicotinate

HRID 1508230Notes

Reaction equation

HRID 1508230 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:16][CH2:17]O>>[CH2:16]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([CH3:11])=[N:10][C:2]=1[Cl:1])[CH3:17]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 1217242-Chloro-6-methylnicotinic acid

Product 1

HCID 15574421Ethyl 2-chloro-6-methylnicotinate

Procedure

A suspension of 2-chloro-6-methylnicotinic acid (7.23 mmol) and 1.2 mL of thionylchloride in 50 mL EtOH were heated to reflux overnight. The mixture was reduced to half of its volume, quenched with sat. aq. NaHCO3 solution and extracted with DCM (2×). The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification by (KP-SIL™ from Biotage) using Hept to Hept/EtOAc (1/1) gives the desired product as colorless oil;

Workup

  1. temperaturewere heated
  2. temperatureto reflux overnight
  3. customquenched with sat. aq. NaHCO3 solution
  4. extractionextracted with DCM (2×)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification by (KP-SIL™ from Biotage)

Sources & evidence

ORD record
ord-aeb8a010ab414dfca5d6c0282b7a4caf
Source dataset
uspto-grants-2015_12
Patent number
US09221832B2

Reaction notes

Loading…