Pentenone → 2,4-Dimethyl-5,6-dimethoxy-8-nitroquinoline

HRID 1863115

反応式

HRID 1863115 の反応式
[CH3:1][O:2][C:3]1[C:9]([O:10][CH3:11])=[CH:8][C:6]([NH2:7])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1.[CH3:15][C:16](=O)[CH:17]=[CH:18][CH3:19]>C1C=CC=CC=1.C(OCC)(=O)C>[CH3:11][O:10][C:9]1[C:3]([O:2][CH3:1])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]2[C:8]=1[C:16]([CH3:15])=[CH:17][C:18]([CH3:19])=[N:7]2

参加物

4

反応物 2

HCID 12248PentenoneHCID 46531524,5-Dimethoxy-2-nitroaniline

生成物 1

HCID 6216122,4-Dimethyl-5,6-dimethoxy-8-nitroquinoline収率 14%

試薬・触媒・溶媒 1

HCID 21583983Benzene ethyl acetate溶媒

実験手順

4,5-Dimethoxy-2-nitroaniline and 3-penten-2-one were subjected to a Skraup reaction. A black, tarry substance was obtained, from which an orange solid could be isolated by chromatography over silica gel using benzene-ethyl acetate (19:1) to elute the product. That material was thrice crystallized from 2-propanol, re-chromatographed, and again crystallized to afford 14% yield of golden 5,6-dimethoxy-2,4-dimethyl-8-nitroquinoline. Although it melted 85°-108°, it showed a single spot on two tlc systems.

後処理

  1. customA black, tarry substance was obtained, from which an orange solid
  2. customcould be isolated by chromatography over silica gel
  3. washto elute the product
  4. customcrystallized from 2-propanol
  5. customre-chromatographed
  6. customagain crystallized

出典と根拠

ORDレコード
ord-39364203104b46139f0635d114ddab03
出典データセット
uspto-grants-1979_09
特許番号
US04167638

関連ノート

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