Acetonitrile → 3-(1-Methyl-1H-pyrrol-2-yl)-3-oxopropanenitrile

HRID 255017Notes

Reaction equation

HRID 255017 reaction equation
CO[C:3]([C:5]1[N:6]([CH3:10])[CH:7]=[CH:8][CH:9]=1)=[O:4].[CH3:11][C:12]#[N:13].CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1>[CH3:10][N:6]1[CH:7]=[CH:8][CH:9]=[C:5]1[C:3](=[O:4])[CH2:11][C:12]#[N:13]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 142178Methyl 1-methylpyrrole-2-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 27771703-(1-Methyl-1H-pyrrol-2-yl)-3-oxopropanenitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-Methyl-1H-pyrrole-2-carboxylic acid methyl ester (5 g, 35.9 mmol) and CH3CN (2.5 mL) were premixed and added into a suspension of potassium tert-butoxide (5.3 g, 47.2 mmol) in 150 mL of dry toluene at 90° C. The mixture was stirred at this temperature overnight. The solid precipitate was collected by filtration, washed with EtOAc and redissolved in 20 mL of water. The resulting solution was acidified with 1 N HCl to approximately pH 1 and was then extracted with EtOAc. The product 3-(1-methyl-1H-pyrrol-2-yl)-3-oxopropionitrile was obtained after removal of the solvent (1.9 g).

Workup

  1. filtrationThe solid precipitate was collected by filtration
  2. washwashed with EtOAc
  3. dissolutionredissolved in 20 mL of water
  4. extractionwas then extracted with EtOAc

Sources & evidence

ORD record
ord-9c7ef8b03ccd4dbc9792ca1842202e21
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

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