2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 21923197, 화합물

HRID 1244849노트

반응식

HRID 1244849 반응식
C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.[C:15]([CH:17]1[CH:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:28]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][C:20]=2[C:19]2[CH2:35][CH2:36][CH2:37][C:18]1=2)#[N:16]>C1(C)C=CC=CC=1>[C:15]([C:17]1[C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:28]2[C:20]([NH:21][C:22]3[C:27]2=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:19]2[CH2:35][CH2:36][CH2:37][C:18]=12)#[N:16]

참가 물질

4

반응물 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 21923192Ethyl 4-cyano-1,2,3,4,5,10-hexahydrocyclopenta[a]carbazole-5-carboxylate

생성물 1

HCID 21923197HCID 21923197, 화합물수율 38%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
20 °C

실험 절차

DDQ (39 mg, 0.17 mmol, 220 mol %) was added to solution of ethyl 4-cyano-1,2,3,4,5,10-hexahydrocyclopenta[a]carbazole-5-carboxylate (24 mg, 0.078 mmol) in toluene (12 mL). The solution immediately turned dark brown, and was stirred at 20° C. for 1.5 hr. The solvent was evaporated. The residue was dissolved in EtOAc and rinsed with dilute aqueous ascorbic acid and twice with saturated NaHCO3. Evaporation of the solvent afforded crude product (21 mg) which was recrystallized from EtOAc gave the product (9 mg, 38% yield) as a beige solid, mp 229–231° C. NMR (CDCl3) δ 8.28 (s, 1H), 7.49 (s, 2H), 7.26 (s, 2H), 4.64 (q, 2H), 3.30 (t, 2H), 3.20 (t, 2H), 2.36 (quintet, 2H), 1.54 (t, 3H).

후처리

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in EtOAc
  3. washrinsed with dilute aqueous ascorbic acid and twice with saturated NaHCO3
  4. customEvaporation of the solvent
  5. customafforded crude product (21 mg) which
  6. customwas recrystallized from EtOAc

출처 및 근거

ORD 기록
ord-bc9ac17994234db49cf2207cfb7da167
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07122679B2

반응 노트

불러오는 중…