1,2-Dichloroethane → 2-Oxo-5-phenyl-1,2-dihydro-pyridine-3-carboxylic acid phenylamide

HRID 2197428Notes

Reaction equation

HRID 2197428 reaction equation
[O:1]=[C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][NH:3]1.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.OC1C2N=NNC=2C=CC=1.CN(C1C=CC=CN=1)C.C(Cl)CCl>O1CCCC1>[C:18]1([NH:17][C:8]([C:7]2[C:2](=[O:1])[NH:3][CH:4]=[C:5]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:6]=2)=[O:10])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 6115AnilineHCID 218852-DimethylaminopyridineHCID 103759752-Hydroxy-5-phenylnicotinic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 586926312-Oxo-5-phenyl-1,2-dihydro-pyridine-3-carboxylic acid phenylamideYield 34.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-Oxo-5-phenyl-1,2-dihydro-pyridine-3-carboxylic acid (44 g, 0.20 mmol) in tetrahydrofuran (5 mL) were successively added aniline (20 μL, 0.23 mmol), hydroxybenzotriazole (30 mg, 0.23 mmol), dimethylaminopyridine (27 mg, 0.23 mmol) and EDC (43 mg, 0.23 mmol). The reaction mixture was stirred at room temperature for 16 hours. The solvent was removed in vacuo and the residue was purified by silica gel chromatography eluting with DCM containing 10% of MeOH to afford the title compound as a white solid (20 mg, 34% yield). MS (ES+) 291. δH (DMSO-d6) 7.2 (3H, m), 7.9 (1H, t), 8.5 (1H, d), 8.6 (2H, m), 9.3 (1H, s).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with DCM containing 10% of MeOH

Sources & evidence

ORD record
ord-c5a35f38d5984366a99cef5653a0e0bb
Source dataset
uspto-grants-2012_12
Patent number
US08338597B2

Reaction notes

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