Ethanol → Ethyl 5,6-Dichloronicotinate

HRID 2065878Notes

Reaction equation

HRID 2065878 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>>[CH2:17]([O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Cl:1])[C:3]([Cl:11])=[N:4][CH:5]=1)[CH3:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 6397ChlorotrimethylsilaneHCID 2479875,6-Dichloronicotinic acid

Product 1

HCID 16762519Ethyl 5,6-Dichloronicotinate

Procedure

A solution of 5,6-dichloronicotinic acid (5.0 g, 26 mmol) in dry EtOH (300 mL) and chlorotrimethylsilane (33 mL, 10 eq.) is stirred at rt for 16 h. The solvent is evaporated, the residue dissolved in ether (200 mL) and washed with a solution of sat. aq. Na2CO3 (75 mL) and brine (50 mL). The org. phase is dried over Na2SO4, filtered and evaporated to give 5,6-dichloronicotinic acid ethyl ester (5.8 g) as a solid; LC-MS: tR=0.96 min, [M+1]+=219.93.

Workup

  1. customThe solvent is evaporated
  2. dissolutionthe residue dissolved in ether (200 mL)
  3. washwashed with a solution of sat. aq. Na2CO3 (75 mL) and brine (50 mL)
  4. dry with materialphase is dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-337e6fc1ba6d419688b932e29039bd02
Source dataset
uspto-grants-2012_10
Patent number
US08288554B2

Reaction notes

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