Hydrochloric Acid → Ethyl 2-(4-carboxybenzamido)-4-propionamidobenzoate

HRID 27473Notes

Reaction equation

HRID 27473 reaction equation
[C:1]([C:4]1[CH:24]=[CH:23][C:7]([C:8]([NH:10][C:11]2[CH:21]=[C:20]([NH2:22])[CH:19]=[CH:18][C:12]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:9])=[CH:6][CH:5]=1)([OH:3])=[O:2].[C:25](Cl)(=[O:28])[CH2:26][CH3:27].O.Cl>N1C=CC=CC=1>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:10][C:11]2[CH:21]=[C:20]([NH:22][C:25](=[O:28])[CH2:26][CH3:27])[CH:19]=[CH:18][C:12]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:9])=[CH:23][CH:24]=1)([OH:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 62324Propionyl chlorideHCID 189795Ethyl 2-(4'-carboxybenzamido)-4-aminobenzoate

Product 1

HCID 6918053Ethyl 2-(4-carboxybenzamido)-4-propionamidobenzoateYield 62.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3 g of ethyl 2-(4-carboxybenzamido)-4-aminobenzoate in 30 ml of pyridine was mixed with 3 g of propionyl chloride, and the mixture was held at 40° to 50° C. for a period of 3 hours. Subsequently, 20 ml of water was gradually added to the mixture which was held at the temperature for a period of one hour. After further addition of 100 ml of water, hydrochloric acid was used to control the pH of the reaction mixture between 1 and 2, and the precipitating crystal was filtered, washed with water, and recrystallized from a solvent mixture of ethanol and water to thereby produce 2.2 g of ethyl 2-(4-carboxybenzamido)-4-propionamidobenzoate having a melting point in the range of from 246° to 248° C.

Workup

  1. waitwas held at the temperature for a period of one hour
  2. filtrationthe precipitating crystal was filtered
  3. washwashed with water
  4. customrecrystallized from a solvent mixture of ethanol and water

Sources & evidence

ORD record
ord-485debda829a454595f8686242c2d0f2
Source dataset
uspto-grants-1980_09
Patent number
US04221814

Reaction notes

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