Ethanol → Ethyl 2-amino-6-chloropyridine-4-carboxylate

HRID 1468284Notes

Reaction equation

HRID 1468284 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[N:10]=1)[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH2:16](O)[CH3:17]>>[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[N:10]=1)[C:5]([O:7][CH2:16][CH3:17])=[O:6]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 2369862-Amino-6-chloropyridine-4-carboxylic acid

Product 1

HCID 269587Ethyl 2-amino-6-chloropyridine-4-carboxylateYield 88%

Procedure

2-Amino-6-chloroisonicotinic acid (500 mg, 2.90 mmol) was dissolved in ethanol (29.0 mL), and the solution was stirred under heat and reflux for 3 hours after adding thionyl chloride (1.06 mL, 14.5 mmol). The solvent was then evaporated under reduced pressure. The residue was extracted with chloroform after adding a sodium hydrogen carbonate aqueous solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give ethyl 2-amino-6-chloroisonicotinate (510 mg, yield 88%).

Workup

  1. temperatureunder heat
  2. temperaturereflux for 3 hours
  3. customThe solvent was then evaporated under reduced pressure
  4. extractionThe residue was extracted with chloroform
  5. additionafter adding a sodium hydrogen carbonate aqueous solution
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b7dfe67725cc407ab9cbcb9e4dc29368
Source dataset
uspto-grants-2015_04
Patent number
US09000186B2

Reaction notes

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