Hydrochloric Acid → 1-Methyl-5-p-toluoylpyrrole 2-acetamidoacetic acid

HRID 483240Notes

Reaction equation

HRID 483240 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=[CH:3]1.C([O:18][C:19](=[O:25])[CH2:20][NH:21][C:22](=[O:24])[CH3:23])C.C(O)C.[OH-].[Na+].Cl>O.C1COCC1>[CH3:1][N:2]1[C:6]([C:7]([C:9]2[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=2)=[O:8])=[CH:5][CH:4]=[CH:3]1.[C:22]([NH:21][CH2:20][C:19]([OH:25])=[O:18])(=[O:24])[CH3:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 867406971-Methyl-5-p-toluoylpyrrole 2-acetamidoacetic acid ethyl ester

Product 1

HCID 867406981-Methyl-5-p-toluoylpyrrole 2-acetamidoacetic acidYield 57.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture consisting of 4.45 grams (0.013 moles) of 1-methyl-5-p-toluoylpyrrole-2-acetamidoacetic acid ethyl ester (1-b), 50 ml of ethanol, 25 ml of THF and 19.5 ml (0.0195 moles) of 1N NaOH was kept under stirring at room temperature (20°-25° C.) for 1.5 hours. The mixture was then diluted with water to 300 ml and slowly acidified with 37% HCl. A solid product precipitated which, after filtration and drying, weighed 3.4 grams and was crystallized from ethanol thus giving 2.3 grams of a compound of formula ##STR23## having the following chemico-physical characteristics: Formula: C17H18N2O4.

Workup

  1. customA solid product precipitated which
  2. filtrationafter filtration
  3. customdrying
  4. customwas crystallized from ethanol

Sources & evidence

ORD record
ord-58f1d67d628c48868c82d3f3b323b9ad
Source dataset
uspto-grants-1986_03
Patent number
US04578481

Reaction notes

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