Tosylmethyl isocyanide → HCID 86627461、化合物

HRID 1969931ノート

反応式

HRID 1969931 の反応式
C1(C)C=CC(S([CH2:10][N+:11]#[C-])(=O)=[O:8])=CC=1.CC(C)([O-])C.[K+].C(O[CH2:24][CH:25]=[C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[NH:28][C:27]1=[O:35])(=O)C>O1CCCC1>[O:35]=[C:27]1[C:26]2[NH:11][CH:10]=[CH:24][C:25]=2[C:34]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[NH:28]1.[CH2:26]([C:27]([O-:35])=[O:8])[CH3:34]

参加物

5

反応物 3

HCID 161915Tosylmethyl isocyanideHCID 23665647Potassium tert-butoxideHCID 68938981(2-Oxo-1,2-dihydro-indol-3-ylidene)-ethyl ethanoate

生成物 1

HCID 86627461HCID 86627461、化合物収率 91.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

18.3 g (93.6 mmol) of p-toluenesulfonylmethyl isonitrile followed by a solution of 54 mL (93.6 mmol) of a 20% solution of potassium tert-butoxide in tetrahydrofuran in 700 mL of anhydrous tetrahydrofuran are added to a solution of 20.3 g (93.6 mmol) of (2-oxo-1,2-dihydro-indol-3-ylidene)-ethyl ethanoate dissolved in 340 mL of anhydrous tetrahydrofuran (time of addition 90 minutes). The reaction mixture is refluxed for 1 hour then the solid is filtered. The filtrate is poured into a mixture of ice and water (about 1 L) and the solution is acidified with acetic acid until the pH is 4. The solvents are concentrated by evaporation under vacuum then the solid is filtered and then recrystallized from acetic acid to give 11.05 g (37%) of 4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate cocrystallized with one equivalent of acetic acid in the form of a white solid.

後処理

  1. temperatureThe reaction mixture is refluxed for 1 hour
  2. filtrationthe solid is filtered
  3. additionThe filtrate is poured into a mixture of ice and water (about 1 L)
  4. concentrationThe solvents are concentrated by evaporation under vacuum
  5. filtrationthe solid is filtered
  6. customrecrystallized from acetic acid

出典と根拠

ORDレコード
ord-7cb282b2e2cb40efab29649e18f03d3c
出典データセット
uspto-grants-2013_04
特許番号
US08426437B2

反応ノート

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