Hydrochloric Acid → 7-(Methylthio)-3-nitroquinoline

HRID 1043780ノート

反応式

HRID 1043780 の反応式
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([NH:9][CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=O)[CH:6]=[CH:7][CH:8]=1.Cl.CSC1C=C(N)C=CC=1.C1(S)C=CC=CC=1>C(O)(=O)C>[CH3:1][S:2][C:3]1[CH:4]=[C:5]2[C:6]([CH:12]=[C:11]([N+:14]([O-:16])=[O:15])[CH:10]=[N:9]2)=[CH:7][CH:8]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 15693Benzenamine, 3-(methylthio)-HCID 72310184HCID 72310184、化合物

生成物 1

HCID 595074907-(Methylthio)-3-nitroquinoline収率 15.6%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a refluxing mixture of 3-[(3-methylthiophenyl)amino]-2-nitroprop-2-enal (2.3 g, 9.6 mmol) and the HCl salt of 3-methylthiophenylamine (2.7 g, 19.3 mmol) in acetic acid (25 mL) was added thiophenol (0.2 g, 1.9 mmol). After being refluxed for 18 h, the mixture was cooled to room temperature and the acetic acid was removed under reduced pressure. To the remaining dark colored solid EtOAc (50 mL) was added with stirring. Filtration gave a yellow/green solid and a dark filtrate. The product crystallized from the EtOAc solution upon standing. Filtration and rinsing with cold EtOAc gave 330 mg crystalline product. The yellow/green solid was washed with 3×250 mL portions of dichloromethane. The dichloromethane washes were concentrated to give an additional 150 mg of product (23%). LC/MS (m/z): 221.1 (MH+), Rt 2.54 minutes.

後処理

  1. temperatureAfter being refluxed for 18 h
  2. customthe acetic acid was removed under reduced pressure
  3. additionTo the remaining dark colored solid EtOAc (50 mL) was added
  4. filtrationFiltration
  5. customgave a yellow/green solid
  6. customThe product crystallized from the EtOAc solution
  7. filtrationFiltration
  8. washrinsing with cold EtOAc

出典と根拠

ORDレコード
ord-69310b88ead343ba94b96489f5141166
出典データセット
uspto-grants-2013_10
特許番号
US08563549B2

反応ノート

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