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

HRID 924581Notes

Reaction equation

HRID 924581 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-4bd21d8a1d4c49ca93d9c0f40f59048a
Source dataset
uspto-grants-2016_03
Patent number
US09281483B2

Reaction notes

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