1,2-Dichloroethane → Ethyl 3-aminopyridine-2-carboxylate

HRID 550362

Reaction equation

HRID 550362 reaction equation
[NH2:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:11](Cl)[CH2:12]Cl>C(O)C.CN(C1C=CN=CC=1)C>[NH2:1][C:2]1[C:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 111,2-DichloroethaneHCID 738363-Aminopicolinic acid

Product 1

HCID 565054Ethyl 3-aminopyridine-2-carboxylateYield 130.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 702EthanolSolvent

Procedure

3-Amino-2-picolinic acid (4.14 g) was suspended in ethanol (100 ml) at room temperature with stirring. DMAP (3.7 g) was added and the reaction was stirred for 1 hour at room temperature. A further equivalent of DMAP (3.7 g) was added and the suspension disappeared, and then EDC (5.80 g) was added and the reaction was stirred at room temperature for 17 hours. The ethanol was evaporated to give a dark oil, water was added and the mixture was extracted with ethyl acetate, washed with brine and dried over magnesium sulphate. Evaporation of the solvent gave ethyl 3-amino-2-picolinate as a solid (6.5 g), mixed in a 2:1 ratio with DMAP.

Workup

  1. stirringthe reaction was stirred for 1 hour at room temperature
  2. stirringthe reaction was stirred at room temperature for 17 hours
  3. customThe ethanol was evaporated
  4. customto give a dark oil, water
  5. additionwas added
  6. extractionthe mixture was extracted with ethyl acetate
  7. washwashed with brine
  8. dry with materialdried over magnesium sulphate
  9. customEvaporation of the solvent

Sources & evidence

ORD record
ord-05ebb534ff354b0da15d4370faf4a9a9
Source dataset
uspto-grants-2011_05
Patent number
US07947679B2

Linked notes

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