4-Aminophenol → 1-Methyl-beta-oxo-alpha-(p-hydroxyphenylcarbamoyl)-2-pyrrolpropionitrile

HRID 127588Notes

Reaction equation

HRID 127588 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=[O:16])[CH:8]([C:11]([O:13]CC)=O)[C:9]#[N:10].[CH:17]1[C:22]([NH2:23])=[CH:21][CH:20]=[C:19]([OH:24])[CH:18]=1>C1(C)C(C)=CC=CC=1>[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=[O:16])[CH:8]([C:11](=[O:13])[NH:23][C:22]1[CH:17]=[CH:18][C:19]([OH:24])=[CH:20][CH:21]=1)[C:9]#[N:10]

Participants

4

Reactant 2

HCID 4034-AminophenolHCID 202854131-Methyl-beta-oxo-alpha-ethoxycarbonyl-2-pyrrolepropionitrile

Product 1

HCID 99939681-Methyl-beta-oxo-alpha-(p-hydroxyphenylcarbamoyl)-2-pyrrolpropionitrile

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

The mixture of 5.7 g of 1-methyl-β-oxo-α-ethoxycarbonyl-2-pyrrolpropionitrile, 3,6 g of p-aminophenol and 300 ml of xylene is refluxed for 2 hours and filtered hot. The filtrate is chilled, the crystals formed collected and recrystallized from methanol, to yield the 1-methyl-β-oxo-α-(p-hydroxyphenylcarbamoyl)-2-pyrrolpropionitrile melting at 182°-184°.

Workup

  1. temperatureis refluxed for 2 hours
  2. filtrationfiltered hot
  3. temperatureThe filtrate is chilled
  4. customthe crystals formed
  5. customcollected
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-1fbb6d3ae0e0441cb4d8de881ca8e099
Source dataset
uspto-grants-1981_03
Patent number
US04256759

Reaction notes

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