Phosphorus oxychloride → 6-Chloro-3-methoxy-5,10-diaza-benzo[c]fluoren-7-one

HRID 1840400Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1840400
COC1C=CC2C3C4C=CN=CC=4C(=O)C=3C(=O)NC=2C=1.[CH3:22][O:23][C:24]1[CH:25]=[CH:26][C:27]2[C:39]3[C:38]4[CH:37]=[N:36][CH:35]=[CH:34][C:33]=4[C:32](=[O:40])[C:31]=3[C:30](=O)[NH:29][C:28]=2[CH:42]=1.P(Cl)(Cl)([Cl:45])=O>>[Cl:45][C:30]1[C:31]2[C:32](=[O:40])[C:33]3[CH:34]=[CH:35][N:36]=[CH:37][C:38]=3[C:39]=2[C:27]2[CH:26]=[CH:25][C:24]([O:23][CH3:22])=[CH:42][C:28]=2[N:29]=1

Komponenten

4

Edukt 3

HCID 24813Phosphorus oxychlorideHCID 111501193-methoxy-5H-5,9-diaza-benzo[c]fluorene-6,7-dioneHCID 114259203-methoxy-5H-5,10-diaza-benzo[c]fluorene-6,7-dione

Produkt 1

HCID 113923176-Chloro-3-methoxy-5,10-diaza-benzo[c]fluoren-7-one

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

The mixture of 3-methoxy-5H-5,9-diaza-benzo[c]fluorene-6,7-dione and 3-methoxy-5H-5,10-diaza-benzo[c]fluorene-6,7-dione (8.77 g) obtained above was suspended in phosphorus oxychloride (359 g) and stirred at 60° C. for three days. Excess phosphorus oxychloride was evaporated under reduced pressure. The residue was treated with ice water and saturated sodium hydrogen carbonate to adjust the pH to about 7. Black ppt was collected with suction and washed water. The ppt was purified by silica gel column chromatography developed by dichloromethane-methanol-trifluoroacetic acid (200:2:1) and by dichloromethane-methanol-trifluoroacetic acid (200:4:1). This chromatography gave two yellow bands. The first band was collected and evaporated. The residue was treated with methanol to give a less polar isomer (1.72 g), 6-chloro-3-methoxy-5,10-diaza-benzo[c]fluoren-7-one (Example 1c-1) as a yellow powder. The second band was collected and evaporated. The residue was treated with methanol to give a more polar isomer (1.86 g), 6-chloro-3-methoxy-5,9-diaza-benzo[c]-fluoren-7-one (Example 1c-2) as a yellow powder.

Aufarbeitung

  1. customobtained
  2. customExcess phosphorus oxychloride was evaporated under reduced pressure
  3. additionThe residue was treated with ice water and saturated sodium hydrogen carbonate
  4. customBlack ppt was collected with suction
  5. washwashed water
  6. customThe ppt was purified by silica gel column chromatography
  7. customThis chromatography gave two yellow bands
  8. customThe first band was collected
  9. customevaporated
  10. additionThe residue was treated with methanol

Quellen und Nachweise

ORD-Eintrag
ord-19ea4e4df81d4b769e9afee8923d3c80
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06680326B2

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