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

HRID 374183

反応式

HRID 374183 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-97f4987ca5814880ad643d1caa6e3ad8
出典データセット
uspto-grants-1992_11
特許番号
US05166347

関連ノート

読み込み中…