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

HRID 1840400노트

반응식

HRID 1840400 반응식
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

참가 물질

4

반응물 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

생성물 1

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

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-19ea4e4df81d4b769e9afee8923d3c80
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06680326B2

반응 노트

불러오는 중…