Phenylglycine nitrile → (2-Pyrrol-1-yl-phenyl)-acetonitrile

HRID 467985

Reaction equation

HRID 467985 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]#[N:10].CO[CH:13]1[CH2:17][CH2:16][CH:15](OC)O1>C(O)(=O)C>[N:1]1([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:8][C:9]#[N:10])[CH:13]=[CH:17][CH:16]=[CH:15]1

Participants

4

Reactant 2

HCID 76307Phenylglycine nitrileHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 12196204(2-Pyrrol-1-yl-phenyl)-acetonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Under inert atmosphere a solution of 500 mg (3.783 mmol) of 2-Aminophenylacetonitrile and 1 mL (7.566 mmol) of 2,5-Dimethoxytetrahydrofuran in 5 mL of acetic acid was heated to 60° C. for 2 hours. After cooling the reaction mixture was concentrated under reduced pressure. The residue was purified by flash chromatography on SiO2 using cyclohexane/ethyl acetate mixture of increasing polarity (from 100% cyclohexane to 100% ethyl acetate) as eluent. The title compound was obtained as a light yellow oil (470 mg, 68.2%).

Workup

  1. temperatureAfter cooling the reaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. customThe residue was purified by flash chromatography on SiO2
  4. additioncyclohexane/ethyl acetate mixture
  5. temperatureof increasing polarity (from 100% cyclohexane to 100% ethyl acetate) as eluent

Sources & evidence

ORD record
ord-fb5b71493632416aa63df853b0a888de
Source dataset
uspto-grants-2014_01
Patent number
US08623901B2

Linked notes

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