Ethanol → Ethyl 5,6-Dichloronicotinate

HRID 1908756Notes

Reaction equation

HRID 1908756 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.[CH2:17](O)[CH3:18]>>[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, 26.0 mmol) in dry ethanol (300 mL) and chlorotrimethylsilane (33 mL, 10 eq.) is stirred at rt for 16 h. The solvent is evaporated, the residue dissolved in diethyl 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 diethyl 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-3bf1e591c0ff4d24b71911f33ca0a64a
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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