Dimethylformamide → Ethyl 6-chloro-5-cyanonicotinate

HRID 1820974Notes

Reaction equation

HRID 1820974 reaction equation
[C:1]([C:3]1[C:4](O)=[N:5][CH:6]=[C:7]([CH:13]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])#[N:2].CN(C=O)C.O=S(Cl)[Cl:22]>>[Cl:22][C:4]1[C:3]([C:1]#[N:2])=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 178469849HCID 178469849, compound

Product 1

HCID 57506169Ethyl 6-chloro-5-cyanonicotinate

Procedure

To a solution of 222 mg (1.16 mmol) of ethyl 5-cyano-6-hydroxynicotinate (from Step A) in 5 mL of SOCl2 was added 500 μL of DMF. After refluxing overnight, the mixture was cooled to rt and concentrated. The residue was dissolved in EtOAc (20 mL) and washed with brine (10 mL), saturated NaHCO3 (10 mL), and brine (10 mL), dried over Na2SO4, and concentrated. Chromatography on a Biotage 40M cartridge using 1:9 v/v EtOAc/hexanes gave 145 mg of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.44 (d, J=7.1, 3H), 4.46 (q, J=7.1, 2H), 8.58 (d, J=2.1, 1H), 9.15 (d, J=2.1, 1H).

Workup

  1. temperatureAfter refluxing overnight
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in EtOAc (20 mL)
  4. washwashed with brine (10 mL), saturated NaHCO3 (10 mL), and brine (10 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-57bf52f7021f455581024ab36c23e1be
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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