N-[1-(1,3,4,9-Tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)ethyl]acetamide → 3,3a,5,6-Tetrahydro-1,3,3a-trimethyl-4-oxa-2,10b-diazafluoranthene

HRID 647593노트

반응식

HRID 647593 반응식
[CH3:1][C:2]1([CH:15]([NH:17][C:18](=O)[CH3:19])[CH3:16])[C:7]2[NH:8][C:9]3[C:14]([C:6]=2[CH2:5][CH2:4][O:3]1)=[CH:13][CH:12]=[CH:11][CH:10]=3>P(Cl)(Cl)(Cl)=O>[CH3:19][C:18]1[N:8]2[C:7]3[C:2]([CH3:1])([O:3][CH2:4][CH2:5][C:6]=3[C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:15]([CH3:16])[N:17]=1

참가 물질

3

반응물 1

HCID 12708188N-[1-(1,3,4,9-Tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)ethyl]acetamide

생성물 1

HCID 127081893,3a,5,6-Tetrahydro-1,3,3a-trimethyl-4-oxa-2,10b-diazafluoranthene

시약·촉매·용매 1

HCID 24813Phosphorus oxychloride용매

실험 절차

A mixture of N-[1-(1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)ethyl]-acetamide (2.0 g, described in Example 2) and phosphorus oxychloride (10 ml) is heated at 100°-110° C. for 3 hours and evaporated. The residue is partioned between chloroform and 10% sodium carbonate. The organic layer is collected, washed with water, saturated brine solution and dried over magnesium sulfate. The residue is chromatographed on silica gel using chloroform. The eluates are evaporated to give a less polar isomer, isomer A(0.40 g), of the title compound, nmr(CDCl3) δ0.86(d) and 3.74(q) and a more polar isomer, isomer B(0.40 g), of the title compound nmr(CDCl3) δ0.78(d) and 4.07(q).

후처리

  1. temperatureis heated at 100°-110° C. for 3 hours
  2. customevaporated
  3. customThe organic layer is collected
  4. washwashed with water, saturated brine solution
  5. dry with materialdried over magnesium sulfate
  6. customThe residue is chromatographed on silica gel
  7. customThe eluates are evaporated
  8. customto give a less polar isomer, isomer A(0.40 g)

출처 및 근거

ORD 기록
ord-63b2fb12e4524b5098a0ae3891d507b2
출처 데이터셋
uspto-grants-1983_10
특허 번호
US04409224

반응 노트

불러오는 중…