Water → 2-(1H-pyrrol-1-yl)benzonitrile

HRID 2363791Notes

Reaction equation

HRID 2363791 reaction equation
[C:1](#[N:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].CO[CH:12]1[CH2:16][CH2:15][CH:14](OC)O1.O>C(O)(=O)C>[N:4]1([C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1]#[N:9])[CH:12]=[CH:16][CH:15]=[CH:14]1

Participants

5

Reactant 3

HCID 962WaterHCID 729132-AminobenzonitrileHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 7073252-(1H-pyrrol-1-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Anthranilonitrile (10.0 grams, 85.0 mmol) was dissolved in 350 mL of acetic acid. To this was added 2,5-dimethoxytetrahydrofuran (11.0 mL, 85.0 mmol). This was stirred at reflux for 2 hours after which time the reaction mixture was pored into water and the product extracted with dichloromethane. The organic layer was washed with water, dried over sodium sulfate and chromatographed on a silica gel column using a mobile phase of 1:1 dichloromethane-hexane to afford the title compound as a white solid. NMR confirms structure.

Workup

  1. temperatureat reflux for 2 hours after which time the reaction mixture
  2. extractionthe product extracted with dichloromethane
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. customchromatographed on a silica gel column

Sources & evidence

ORD record
ord-b38ed8ae04f749a2be63bba8d0abf5c8
Source dataset
uspto-grants-2014_04
Patent number
US08691988B2

Reaction notes

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