Dimethyl malonate → Dimethyl (alpha-amino-3-nitrobenzylidene)malonate

HRID 981151ノート

反応式

HRID 981151 の反応式
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[N+:10]([C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#[N:17])([O-:12])=[O:11]>ClCCCl>[NH2:17][C:16](=[C:2]([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4])[C:15]1[CH:18]=[CH:19][CH:20]=[C:13]([N+:10]([O-:12])=[O:11])[CH:14]=1

参加物

4

反応物 2

HCID 7943Dimethyl malonateHCID 120793-Nitrobenzonitrile

生成物 1

HCID 9970879Dimethyl (alpha-amino-3-nitrobenzylidene)malonate収率 65.8%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

To a mixture of dimethyl malonate (100 g) and 3-nitrobenzonitrile (112 g) in 1,2-dichloroethane (500 ml) was added stannic chloride (177 g) at once with a syringe and refluxed for 1 hour with stirring. The white precipitates were collected by filtration, dissolved in a mixture of acetone (2 l) and water (2 l) and adjusted to pH 9.0 with 20% aqueous sodium hydroxide. The resulting white solid was filtered off, and the filtrate was extracted with methylene chloride (2 l). The extract was washed with saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated in vacuo. The resulting precipitates were recrystallized from a mixture of diethyl ether and methylene chloride to give dimethyl (α-amino-3-nitrobenzylidene)malonate (139.5 g).

後処理

  1. temperaturerefluxed for 1 hour
  2. customThe white precipitates
  3. filtrationwere collected by filtration
  4. dissolutiondissolved in a mixture of acetone (2 l) and water (2 l)
  5. filtrationThe resulting white solid was filtered off
  6. extractionthe filtrate was extracted with methylene chloride (2 l)
  7. washThe extract was washed with saturated aqueous sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. customevaporated in vacuo
  10. customThe resulting precipitates
  11. customwere recrystallized from a mixture of diethyl ether and methylene chloride

出典と根拠

ORDレコード
ord-1c7c93751cc44407acb48d0aa815c7d4
出典データセット
uspto-grants-1991_02
特許番号
US04990507

反応ノート

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