2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Dimethyl 4-ethyl-6-methoxy-3-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizine-1,2-dicarboxylate

HRID 1421263노트

반응식

HRID 1421263 반응식
[CH2:1]([C:3]1[C:4]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][N:6]2[C:11]=1[CH:10]=[C:9]([O:12][CH3:13])[CH:8]=[CH:7]2)[CH3:2].[C:22]([C:28]([O:30][CH3:31])=[O:29])#[C:23][C:24]([O:26][CH3:27])=[O:25].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[CH2:1]([C:3]1[C:11]2[N:6]3[C:7]([CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)=[C:23]([C:24]([O:26][CH3:27])=[O:25])[C:22]([C:28]([O:30][CH3:31])=[O:29])=[C:5]3[C:4]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[CH3:2]

참가 물질

5

반응물 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 12980Dimethyl acetylenedicarboxylateHCID 11108777HCID 11108777, 화합물

생성물 1

HCID 11825967Dimethyl 4-ethyl-6-methoxy-3-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizine-1,2-dicarboxylate수율 92%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A solution of 1-ethyl-7-methoxy-2-(4-methoxyphenyl)indolizine (25.0 g, 0.089 mol) in 800 ml of toluene was stirred in an ice bath, while dimethyl acetylenedicarboxylate (12.6 ml, 0.103 mol) was added dropwise. When the starting material had been consumed according to TLC, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (21.18 g, 0.093 mol) was added in portions. When the addition was complete, the mixture was refluxed for one hour. The resulting hydroquinone was filtered off, and the filtrate was concentrated to dryness. The residue was triturated with petroleum ether (40-60) and isolated to afford 33.8 g (92%) of the title compound. M.p. 153-5° C. 1H-NMR (DMSO-d6, 200 MHz) δ: 1.36 (t, 3H), 3.07 (q, 2H), 3.76 (s, 3H), 3.86 (s, 3H), 3.89 (s, 3H), 4.10 (s, 3H), 7.15 (d, 2H), 7.53 (d, 2H), 7.84 (d, 1H), 8.00 (d, 1H). (Compound 1).

후처리

  1. additionwas added dropwise
  2. customWhen the starting material had been consumed
  3. additionwas added in portions
  4. additionWhen the addition
  5. temperaturethe mixture was refluxed for one hour
  6. filtrationThe resulting hydroquinone was filtered off
  7. concentrationthe filtrate was concentrated to dryness
  8. customThe residue was triturated with petroleum ether (40-60)
  9. customisolated

출처 및 근거

ORD 기록
ord-090fe8e5960b4846bf0b59ae15177ac6
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06075036

반응 노트

불러오는 중…