Benzocaine → ethyl 4-(pyridine-3-carbonylamino)benzoate

HRID 362328Notes

Reaction equation

HRID 362328 reaction equation
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.[NH2:11][C:12]1[CH:22]=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][CH:13]=1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl>[N:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:21][CH:22]=2)=[O:9])[CH:4]=1

Participants

6

Reactant 3

HCID 2337BenzocaineHCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)

Product 1

HCID 279888ethyl 4-(pyridine-3-carbonylamino)benzoateYield 85.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.83 g (0.01 mol) of nicotinoyl chloride hydrochloride (97%), 1.65 g of (0.01 mol) of ethyl 4-aminobenzoate, 2.22 g (0.022 mol) of triethylamine and 61 mg of 4-dimethylaminopyridine in 33 ml of dichloromethane is refluxed 24 hours. The solution is washed with water, 2N citric acid and NaHCO3 solution. The solvent is removed and the residue triturated with methanol to give 2.3 g of ethyl 4-[(3-pyridinylcarbonyl)amino]benzoate as yellow crystals, m.p. 125°-127° C.

Workup

  1. temperatureis refluxed 24 hours
  2. washThe solution is washed with water, 2N citric acid and NaHCO3 solution
  3. customThe solvent is removed
  4. customthe residue triturated with methanol

Sources & evidence

ORD record
ord-414e9a91cd3844ab877861c6b7265bc9
Source dataset
uspto-grants-1999_02
Patent number
US05869483

Reaction notes

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