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

HRID 981151노트

반응식

HRID 981151 반응식
[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

참가 물질

4

반응물 2

HCID 7943Dimethyl malonateHCID 120793-Nitrobenzonitrile

생성물 1

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

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1c7c93751cc44407acb48d0aa815c7d4
출처 데이터셋
uspto-grants-1991_02
특허 번호
US04990507

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