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Ammonia → 4-(4-Chlorobenzyloxy)-1-(3-(methylamino)-4-nitrophenyl)pyridin-2(1h)-one

HRID 2202913
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HRID 2202913 반응식
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][NH:11][C:10](=[O:14])[CH:9]=2)=[CH:4][CH:3]=1.Br[C:18]1[CH:19]=[CH:20][C:21]([N+:26]([O-:28])=[O:27])=[C:22]([CH:25]=1)[NH:23][CH3:24].CNCCNC.C(=O)([O-])[O-].[K+].[K+].N>[Cu](I)I.CS(C)=O>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][N:11]([C:18]3[CH:19]=[CH:20][C:21]([N+:26]([O-:28])=[O:27])=[C:22]([NH:23][CH3:24])[CH:25]=3)[C:10](=[O:14])[CH:9]=2)=[CH:4][CH:3]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 222AmmoniaHCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 106095305-bromo-N-methyl-2-nitroanilineHCID 574978644-[(4-Chlorophenyl)methoxy]pyridin-2(1H)-one

생성물 1

HCID 896911684-(4-Chlorobenzyloxy)-1-(3-(methylamino)-4-nitrophenyl)pyridin-2(1h)-one
수율 73.3%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 679Dimethyl Sulfoxide용매

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온도
150 °C

실험 절차

A mixture of 4-((4-chlorobenzyl)oxy)pyridin-2(1H)-one (10 g), 5-bromo-N-methyl-2-nitroaniline (9.80 g), N,N′-dimethylethylenediamine (4.76 ml), copper iodide (8.08 g), potassium carbonate (17.59 g) and DMSO (200 ml) was heated at 150° C. for 2 h. The mixture was poured into 28% NH3 solution. The resulting precipitate was collected and washed with IPA. The solid was dissolved in DMSO (100 ml) at 80° C., and allowed to cool to room temperature to give a precipitate. After filtration, the precipitate was washed with IPA and dried to give the title compound (12 g) as a yellow solid.

후처리

  1. customThe resulting precipitate was collected
  2. washwashed with IPA
  3. dissolutionThe solid was dissolved in DMSO (100 ml) at 80° C.
  4. temperatureto cool to room temperature
  5. customto give a precipitate
  6. filtrationAfter filtration
  7. washthe precipitate was washed with IPA
  8. customdried

출처 및 근거

ORD 기록
ord-982af0a26e344a98bac3ee14ed7821f9
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09365540B2

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