Aniline → Prinomide

HRID 127587

Reaction equation

HRID 127587 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].[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=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:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:9]#[N:10]

Participants

4

Reactant 2

HCID 6115AnilineHCID 202854131-Methyl-beta-oxo-alpha-ethoxycarbonyl-2-pyrrolepropionitrile

Product 1

HCID 60352Prinomide

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

The mixture of 1.1 g of 1-methyl-β-oxo-α-ethoxycarbonyl-2-pyrrolpropionitrile, 1.1 g of aniline and 60 ml of xylene, is refluxed for 41/2 hours. After standing and cooling to room temperature overnight, the solution is filtered, evaporated and the residue recrystallized from methanol, to yield the 1-methyl-β-oxo-α-phenylcarbamoyl-2-pyrrolpropionitrile melting at 173°-174°; it is identical with that obtained according to Example 1.

Workup

  1. temperatureis refluxed for 41/2 hours
  2. filtrationthe solution is filtered
  3. customevaporated
  4. customthe residue recrystallized from methanol

Sources & evidence

ORD record
ord-92b9856cc49644c097908df62f3abed0
Source dataset
uspto-grants-1981_03
Patent number
US04256759

Linked notes

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