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

HRID 232568Notes

Reaction equation

HRID 232568 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-propylpridine-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 crystallisation from ethyl acetate to give the product as a light brown solid (1.36 g, 60%), 129°-131° C. Found: C,66.29; H,6.53; N,12.78. C18H21N3O3 requires C,66.04; H,6.47; N,12.84%.

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 crystallisation from ethyl acetate

Sources & evidence

ORD record
ord-bcf64b4dd2374c2b941045562bea53b1
Source dataset
uspto-grants-1997_01
Patent number
US05591742

Reaction notes

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