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 1660340ノート

反応式

HRID 1660340 の反応式
[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

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 24813Phosphorus oxychloride溶媒

実験手順

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) δ 0.86 (d) and 3,74 (q) and a more polar isomer, isomer B(0.40 g), of the title compound nmr(CDCl3) δ 0.78 (d) and 4.07 (q).

後処理

  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)

出典と根拠

ORDレコード
ord-e15ab6853da24d0bbc644b2cfd88ee36
出典データセット
uspto-grants-1981_12
特許番号
US04307234

反応ノート

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