Ethanol, 2-amino-, 1-nitrate, nitrate (1:1) → N-cyano-N'-(2-nitroxyethyl)-3-quinolinecarboximidamide

HRID 374183

반응식

HRID 374183 반응식
[C:1]([N:3]=[C:4]([C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)OC)#[N:2].[N+]([O-])(O)=O.[O:21]([CH2:25][CH2:26][NH2:27])[N+:22]([O-:24])=[O:23].C[O-].[Na+]>CO>[C:1]([NH:3][C:4]([C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:27][CH2:26][CH2:25][O:21][N+:22]([O-:24])=[O:23])#[N:2]

참가 물질

5

반응물 3

HCID 78397Ethanol, 2-amino-, 1-nitrate, nitrate (1:1)HCID 10058988Methyl N-cyano-3-quinolinecarboximidateHCID 10942334Sodium Methoxide

생성물 1

HCID 10424050N-cyano-N'-(2-nitroxyethyl)-3-quinolinecarboximidamide수율 54%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Methyl N-cyano-3-quinolinecarboximidate (0.32 g, 1.5 mmol) was dissolved in methanol (3 ml), 2-nitroxyethylamine nitrate (0.42 g, 2.5 mmol) and sodium methoxide (0.12 g, 2.2 mmol) were added. The mixture was stirred at room temperature for 18 hours. After the reaction was completed, the reaction solution was concentrated under reduced pressure, and the residue thus obtained was subjected to chromatography on a silica gel column (WAKO GEL C-200, 30 g) eluting with dichloromethane-methanol (50:1). The eluted fractions were concentrated under reduced pressure and crystallized from dichloromethane-diethyl ether to give the title compound (0.23 g, 0.80 mmol, yield: 54%) as colorless crystals.

후처리

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. customthe residue thus obtained
  3. washeluting with dichloromethane-methanol (50:1)
  4. concentrationThe eluted fractions were concentrated under reduced pressure
  5. customcrystallized from dichloromethane-diethyl ether

출처 및 근거

ORD 기록
ord-97f4987ca5814880ad643d1caa6e3ad8
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05166347

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