Sulfuric Acid → HCID 22116073, compound

HRID 1885630Notes

Reaction equation

HRID 1885630 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][CH:14]([CH2:16][O:17][C:18]3[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=3)[CH2:13][C:12]2=[O:28])=[CH:7][CH:6]=1)(=O)C.S(=O)(=O)(O)O>CO>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][CH:14]([CH2:16][O:17][C:18]3[CH:19]=[CH:20][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:26][CH:27]=3)[CH2:13][C:12]2=[O:28])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 22116035HCID 22116035, compound

Product 1

HCID 22116073HCID 22116073, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-[1-(4-acetylaminophenyl)-2-pyrrolidon-4-yl]methoxybenzoate (1.70 g) is dissolved in methanol (30 ml) and thereto is added conc. sulfuric acid (0.24 ml). The mixture is stirred under refluxing for 23 hours. Subsequently, the reaction solution is concentrated under reduced pressure, and water and the neutralization amount of sodium hydrogen carbonate are added to the resulting residue. The precipitated crystal is collected by filtration and washed with water to give the desired product (1.47 g), m.p. 136°-138° C.

Workup

  1. temperatureunder refluxing for 23 hours
  2. concentrationSubsequently, the reaction solution is concentrated under reduced pressure, and water
  3. additionthe neutralization amount of sodium hydrogen carbonate are added to the resulting residue
  4. filtrationThe precipitated crystal is collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-a5f5528d5f03410f89e5f42cd2166904
Source dataset
uspto-grants-1992_09
Patent number
US05145865

Reaction notes

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