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

HRID 2095183Notes

Reaction equation

HRID 2095183 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-4a75ae0a1be849478b4e1f9529bbc149
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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