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

HRID 1618471Notes

Reaction equation

HRID 1618471 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-2d64833588834cce8fda21666a612a9d
Source dataset
uspto-grants-2014_07
Patent number
US08766529B2

Reaction notes

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