Acetic Acid → 2-(1H-pyrrol-1-yl)benzonitrile

HRID 1270079Notes

Reaction equation

HRID 1270079 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].CO[CH:12]1[CH2:16][CH2:15][CH:14](OC)O1.C(O)(=O)C>C(OCC)(=O)C>[C:4]([C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[N:1]1[CH:12]=[CH:16][CH:15]=[CH:14]1)#[N:5]

Participants

5

Reactant 3

HCID 176Acetic Acid2×HCID 729132-AminobenzonitrileHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-aminobenzonitrile (0.01 mole), 2,5-dimethoxytetrahydrofuran (0.01 mole) and glacial acetic acid (10 ml) was heated under reflux for 30 minutes (TLC check). The acetic acid and ethyl acetate formed was evaporated off and the residue was purified using flash chromatography on silica gel (eluent: CH2Cl2). The pure fraction was recrystallized from the appropriate solvent (mostly ethanol).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes (TLC check)
  3. customwas evaporated off
  4. customthe residue was purified
  5. customThe pure fraction was recrystallized from the appropriate solvent (mostly ethanol)

Sources & evidence

ORD record
ord-ad1fedd2a55b4221817dc89557c2330f
Source dataset
uspto-grants-2007_04
Patent number
US07202240B2

Reaction notes

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