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 647593Notes

Reaction equation

HRID 647593 reaction equation
[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

Participants

3

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-63b2fb12e4524b5098a0ae3891d507b2
Source dataset
uspto-grants-1983_10
Patent number
US04409224

Reaction notes

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