Acetic Acid → Ethyl-alpha-carbethoxy-4-dimethylamino-2-nitrocinnamate

HRID 868331

반응식

HRID 868331 반응식
[CH3:1][N:2]([CH3:14])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[C:5]([N+:11]([O-:13])=[O:12])[CH:4]=1.[C:15]([O:23][CH2:24][CH3:25])(=[O:22])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1>[CH2:20]([O:19][C:17](=[O:18])[C:16]([C:15]([O:23][CH2:24][CH3:25])=[O:22])=[CH:7][C:6]1[CH:9]=[CH:10][C:3]([N:2]([CH3:14])[CH3:1])=[CH:4][C:5]=1[N+:11]([O-:13])=[O:12])[CH3:21]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 7761Diethyl MalonateHCID 8082PiperidineHCID 2913524-Dimethylamino-2-nitrobenzaldehyde

생성물 1

HCID 14365894Ethyl-alpha-carbethoxy-4-dimethylamino-2-nitrocinnamate수율 6.2%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of 89 g (0.5 mol) of 4-dimethylamino-2-nitrobenzaldehyde [H. Baumann, et al German Pat. 2,363,458], 237 g (1.4 mol) of diethyl malonate, 3.44 g (40.4 mmol) of piperidine and 2.43 g (40.4 mmol) of acetic acid in 400 mL of toluene was refluxed for 16 hours under argon, with a Dean Stark trap attached. The solution was cooled to room temperature and washed with 200 mL of 5% aqueous KOH. The organic phase was separated, dried over sodium sulfate (Na2SO4), filtered, and the solvent evaporated. The dark red solid residue was dissolved in 40 mL of CH2Cl2 and 100 mL of hexane added. After standing for 1 hour, the solution was filtered to yield 10.4 g of orange crystals. Recrystallization from CH2Cl2 - hexane produced an analytical sample, m.p. 101°-102° C.

후처리

  1. temperaturewas refluxed for 16 hours under argon, with a Dean Stark trap
  2. washwashed with 200 mL of 5% aqueous KOH
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulfate (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. dissolutionThe dark red solid residue was dissolved in 40 mL of CH2Cl2
  8. addition100 mL of hexane added
  9. filtrationthe solution was filtered

출처 및 근거

ORD 기록
ord-d5c910ee5e9a42a48eed10b2f3fbdf7b
출처 데이터셋
uspto-grants-1988_10
특허 번호
US04778893

연결된 노트

불러오는 중…