9-Methoxyellipticine → 9-Hydroxyellipticine

HRID 442478Notes

Reaction equation

HRID 442478 reaction equation
[CH3:1][C:2]1[C:7]2[CH:8]=[CH:9][N:10]=[CH:11][C:6]=2[C:5]([CH3:12])=[C:4]2[C:13]3[CH:19]=[C:18]([O:20]C)[CH:17]=[CH:16][C:14]=3[NH:15][C:3]=12.Cl.N1C=CC=CC=1>>[CH3:1][C:2]1[C:7]2[CH:8]=[CH:9][N:10]=[CH:11][C:6]=2[C:5]([CH3:12])=[C:4]2[C:13]3[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][C:14]=3[NH:15][C:3]=12

Participants

3

Reactant 2

HCID 725129-MethoxyellipticineHCID 10176127Pyridinium chloride

Product 1

HCID 916439-Hydroxyellipticine

Procedure

A mixture of one part by weight 9-methoxy-ellipticine obtained by extraction from "yellowwood" (Ochrosia maculata) from the island of Reunion, and from 3 to 11 parts by weight of pyridine hydrochloride were heated with gentle reflux for 30 to 90 minutes. The reaction mass became a dark brown colour; it was then poured over crushed ice, the precipitate formed was centrifuged and washed several times with iced water and then recrystallized in methanol. The crystals obtained were orange coloured.

Workup

  1. customobtained by extraction from "yellowwood" (Ochrosia maculata) from the island of Reunion
  2. temperaturewith gentle reflux for 30 to 90 minutes
  3. additionit was then poured
  4. customover crushed ice
  5. customthe precipitate formed
  6. washwashed several times with iced water
  7. customrecrystallized in methanol
  8. customThe crystals obtained

Sources & evidence

ORD record
ord-a4c485deba48447784cab105e97a569c
Source dataset
uspto-grants-1977_08
Patent number
US04045565

Reaction notes

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