Benzoyl chloride → Ethyl 2-benzamidoisonicotinate

HRID 714273Notes

Reaction equation

HRID 714273 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][N:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>N1C=CC=CC=1>[C:13]([NH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][N:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 7015521Ethyl 2-aminopyridine-4-carboxylate

Product 1

HCID 67079544Ethyl 2-benzamidoisonicotinateYield 83%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of ethyl 2-aminoisonicotinate (1.00 g, 6.02 mmol) in anhydrous pyridine (13 mL) was added benzoyl chloride (0.77 mL, 6.63 mmol) dropwise at 0° C. under nitrogen atmosphere. The resulting solution was warmed to ambient temperature, stirred for 18 hours and concentrated in vacuo. The residue was dissolved in ethyl acetate (75 mL), washed with 2 M aqueous hydrochloric acid solution (20 mL) and saturated aqueous sodium bicarbonate solution (20 mL). The organic solution was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluted with 10-50% ethyl acetate in hexanes to give ethyl 2-benzamidoisonicotinate as a colorless solid (1.35 g, 83%): 1H NMR (300 MHz, CDCl3) δ 8.94 (s, 1H), 8.84 (br s, 1H), 8.43 (d, J=5.1 Hz, 1H), 7.98-7.93 (m, 2H), 7.70-7.47 (m, 4H), 4.44 (q, J=7.1 Hz, 2H), 1.43 (t, J=7.1 Hz, 3H); MS (ES+) m/z 271.5 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate (75 mL)
  3. washwashed with 2 M aqueous hydrochloric acid solution (20 mL) and saturated aqueous sodium bicarbonate solution (20 mL)
  4. dry with materialThe organic solution was dried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography
  8. washeluted with 10-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-ae9c1236d73b499a82e6e9166d876e95
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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