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

HRID 376743

反応式

HRID 376743 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-eb99e31f8890430682995e3849a331e9
出典データセット
uspto-grants-2000_02
特許番号
US06022379

関連ノート

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