N-methyl-4-nitrophenethylamine → N-Methyl-N-(6-nitroquinol-2-ylmethyl)-4-nitrophenethylamine

HRID 345037

반응식

HRID 345037 반응식
[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.Cl[CH2:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[C:21]([N+:26]([O-:28])=[O:27])[CH:22]=2)[N:17]=1>C(O)C>[CH3:1][N:2]([CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)[CH2:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[C:21]([N+:26]([O-:28])=[O:27])[CH:22]=2)[N:17]=1

참가 물질

4

반응물 2

HCID 2794239N-methyl-4-nitrophenethylamineHCID 126651392-(Chloromethyl)-6-nitroquinoline

생성물 1

HCID 19813438N-Methyl-N-(6-nitroquinol-2-ylmethyl)-4-nitrophenethylamine

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

N-Methyl-4-nitrophenethylamine (0.39 g, 2.15 mmole) and 2-chloromethyl-6-nitroquinoline (0.40 g, 2.1 mmole) were heated at reflux temperature in ethanol (30 ml) for 6 hours. The solvent was then evaporated and the residue diluted with 2M hydrochloric acid and extracted with methylene chloride. The aqueous layer was basified with aqueous sodium carbonate (to pH ~12) and extracted three times with methylene chloride. These latter organic extracts were combined, dried (MgSO4) and evaporated giving an oil which was purified by column chromatography on silica eluting with methylene chloride containing methanol (0% up to 1%). The product-containing fractions were combined and evaporated to give a solid which was recrystallised from ethanol to give the title compound, yield 0.21 g, m.p. 104°-105°.

후처리

  1. customThe solvent was then evaporated
  2. additionthe residue diluted with 2M hydrochloric acid
  3. extractionextracted with methylene chloride
  4. extractionextracted three times with methylene chloride
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customgiving an oil which
  8. customwas purified by column chromatography on silica eluting with methylene chloride
  9. additioncontaining methanol (0% up to 1%)
  10. customevaporated
  11. customto give a solid which
  12. customwas recrystallised from ethanol

출처 및 근거

ORD 기록
ord-f7d9d487619f446dbc231e356ccf31a5
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05055473

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