p-Toluenesulfonic acid → 3-[2-(1,4-Dioxo-1,4-dihydronaphthalen-2-yl)pyrrol-1-yl]propionitrile

HRID 376743

Reaction equation

HRID 376743 reaction equation
[C:1]1(=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH:3]=[CH:2]1.[N:13]1([CH2:18][CH2:19][C:20]#[N:21])[CH:17]=[CH:16][CH:15]=[CH:14]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[O:12]=[C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH:3]=[C:2]1[C:14]1[N:13]([CH2:18][CH2:19][C:20]#[N:21])[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 85301,4-NaphthoquinoneHCID 965273-(Pyrrol-1-yl)propiononitrile

Product 1

HCID 108023953-[2-(1,4-Dioxo-1,4-dihydronaphthalen-2-yl)pyrrol-1-yl]propionitrileYield 42%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

6.32 millimol of 1,4-naphthoquinone and 3.16 millimol of 3-(1-pyrrolyl) propionitrile were stirred in 50 ml of chloroform in a round-bottomed flask for 5 hours at room temperature, the reaction being catalysed by addition of a few milligrams of para-toluenesulphonic acid. The reaction medium was diluted with 50 ml of chloroform and then washed four times with 50 ml of water and finally with saturated aqueous NaCl solution. The resulting organic phase was dried over Na2SO4 and then concentrated under vacuum. The product 3-[2-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)pyrrol-1-yl]propionitrile was thus isolated in a yield of 42% after purification by chromatography on a column of silica.

Workup

  1. washwashed four times with 50 ml of water
  2. dry with materialThe resulting organic phase was dried over Na2SO4
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-eb99e31f8890430682995e3849a331e9
Source dataset
uspto-grants-2000_02
Patent number
US06022379

Linked notes

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