Pyridine → 2-(Acetoxyacetylamino)-6-methoxybenzamide

HRID 2248757Notes

Reaction equation

HRID 2248757 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:3]=1[C:4]([NH2:6])=[O:5].N1C=CC=CC=1.[C:19]([O:22][CH2:23][C:24](Cl)=[O:25])(=[O:21])[CH3:20]>C(Cl)Cl>[C:19]([O:22][CH2:23][C:24]([NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:3]=1[C:4]([NH2:6])=[O:5])=[O:25])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 26297Acetoxyacetyl chlorideHCID 122648142-Amino-6-methoxybenzamide

Product 1

HCID 149862802-(Acetoxyacetylamino)-6-methoxybenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-6-methoxybenzamide (1.7 g) in methylene chloride (20 ml) is added pyridine (1.6 ml), and thereto is added dropwise acetoxyacetyl chloride (1.1 ml) which is cooled in an ice bath. The mixture is stirred at room temperature for 2 hours, and thereafter, the solvent is distilled off under reduced pressure. The resulting crude crystals are washed with water and then are recrystallized from ethanol to give the title compound (2.1 g) having the following physical properties.

Workup

  1. temperatureis cooled in an ice bath
  2. distillationthe solvent is distilled off under reduced pressure
  3. washThe resulting crude crystals are washed with water
  4. customare recrystallized from ethanol

Sources & evidence

ORD record
ord-ee236f99edf1451e846e3f82c68aa3f2
Source dataset
uspto-grants-1991_08
Patent number
US05041462

Reaction notes

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