2-Ethoxybenzoyl chloride → 3-(2-Ethoxybenzoylamino)-4-n-propylpridine-2-carboxamide

HRID 1936698Notes

Reaction equation

HRID 1936698 reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6](Cl)=[O:7])[CH3:2].[NH2:13][C:14]1[C:15]([C:23]([NH2:25])=[O:24])=[N:16][CH:17]=[CH:18][C:19]=1[CH2:20][CH2:21][CH3:22]>N1C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([NH:13][C:14]1[C:15]([C:23]([NH2:25])=[O:24])=[N:16][CH:17]=[CH:18][C:19]=1[CH2:20][CH2:21][CH3:22])=[O:7])[CH3:2]

Participants

4

Reactant 2

HCID 30163972-Ethoxybenzoyl chlorideHCID 537749353-Amino-4-n-propylpridine-2-carboxamide

Product 1

HCID 541249833-(2-Ethoxybenzoylamino)-4-n-propylpridine-2-carboxamideYield 60%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Ethoxybenzoyl chloride (2.96 g, 0.016 mol) was added dropwise to a stirred solution of 3-amino-4-n-propylpyridine-2-carboxamide (Preparation 6; 1.43 g, 0.008 mol) in pyridine (40 ml) at 0° C. The mixture was stirred at ambient temperature for 4 hours and then the solvent evaporated under vacuum. The residue was dissolved in dichloromethane (100 ml), the solution washed with saturated aqueous sodium carbonate solution (100 ml) and the aqueous phase then washed with dichloromethane (2×25 ml). The combined organic extracts were dried (MgSO4) and evaporated under vacuum, then the residue purified by chromatography on silica gel (15 g), using a methanol in dichloromethane elution gradient (0-3% methanol), followed by crystallization from ethyl acetate to give the product as a light brown solid (1.36 g, 60%), 129-131° C.

Workup

  1. customthe solvent evaporated under vacuum
  2. dissolutionThe residue was dissolved in dichloromethane (100 ml)
  3. washthe solution washed with saturated aqueous sodium carbonate solution (100 ml)
  4. washthe aqueous phase then washed with dichloromethane (2×25 ml)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. customevaporated under vacuum
  7. customthe residue purified by chromatography on silica gel (15 g)
  8. washa methanol in dichloromethane elution gradient (0-3% methanol)
  9. customfollowed by crystallization from ethyl acetate

Sources & evidence

ORD record
ord-f67c4ae008a64fff8fec54da9cec0caf
Source dataset
uspto-grants-2002_05
Patent number
US06391885B1

Reaction notes

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