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

HRID 1863115

반응식

HRID 1863115 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 21583983Benzene ethyl acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-39364203104b46139f0635d114ddab03
출처 데이터셋
uspto-grants-1979_09
특허 번호
US04167638

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