Ethyl 2-aminopyridine-3-carboxylate → 2-[2-(2,4,6-Trifluorophenyl)-acetylamino]-nicotinic acid ethyl ester

HRID 550357Notes

Reaction equation

HRID 550357 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1[NH2:11])[CH3:2].[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[C:15]=1[CH2:22][C:23](Cl)=[O:24]>C1(C)C=CC=CC=1.C(OCC)C>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1[NH:11][C:23](=[O:24])[CH2:22][C:15]1[C:16]([F:21])=[CH:17][C:18]([F:20])=[CH:19][C:14]=1[F:13])[CH3:2]

Participants

5

Reactant 2

HCID 12433260Ethyl 2-aminopyridine-3-carboxylateHCID 574280152,4,6-Trifluorophenylacetyl chloride

Product 1

HCID 586172322-[2-(2,4,6-Trifluorophenyl)-acetylamino]-nicotinic acid ethyl esterYield 93%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

2-Aminonicotinic acid ethyl ester (2.4 g) was suspended in dry toluene (50 ml). To the stirred suspension, 2,4,6-trifluorophenylacetyl chloride (3.0 g) in dry toluene (20 ml) was added. The resulting suspension was heated to reflux for 8 hours. The reaction mixture was cooled to ambient temperature, diluted with diethyl ether (100 ml), washed with water and brine, and the organic layer was dried over magnesium sulphate. The solvent was evaporated to give 2-[2-(2,4,6-trifluorophenyl)-acetylamino]-nicotinic acid ethyl ester as a yellow solid (4.5 g, 93%).

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux for 8 hours
  3. washwashed with water and brine
  4. dry with materialthe organic layer was dried over magnesium sulphate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-809b9c4f66de4e5d932ec0565894e101
Source dataset
uspto-grants-2011_05
Patent number
US07947679B2

Reaction notes

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