Dimethylformamide → HCID 23448016, compound

HRID 1840404Notes

Reaction equation

HRID 1840404 reaction equation
COC1C2N[C:10](=[O:21])C3C(=O)C4N=CC=CC=4C=3C=2C=CC=1.CO[C:24]1[C:29]2[NH:30][C:31](=O)[C:32]3[C:33](=[O:41])[C:34]4[CH:35]=[CH:36][CH:37]=[N:38][C:39]=4[C:40]=3[C:28]=2[CH:27]=[CH:26][CH:25]=1.CN(C=O)C.P(Cl)(Cl)([Cl:50])=O>>[Cl:50][C:31]1[C:32]2[C:33](=[O:41])[C:34]3[CH:35]=[CH:36][CH:37]=[N:38][C:39]=3[C:40]=2[C:28]2[CH:27]=[CH:26][C:25]([O:21][CH3:10])=[CH:24][C:29]=2[N:30]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 23448041HCID 23448041, compoundHCID 23448043HCID 23448043, compound

Product 1

HCID 23448016HCID 23448016, compound

Procedure

The mixture of 4-methoxy-5H-5,8-diaza-benzo[c]fluorene-6,7-dione and 4-methoxy-5H-5,11-diaza-benzo[c]fluorene-6,7-dione (54 mg) obtained above and DMF (0.1 ml) were suspended in phosphorus oxychloride (2 ml) and refluxed for three hours. Excess phosphorus oxychloride was evaporated under reduced pressure. The residue was treated with water and saturated sodium hydrogen carbonate to adjust the pH about 7. Orange ppt was collected with suction and washed water. The ppt was purified by silica gel column chromatography developed by dichloromethane-methanol (200:1) and by dichloromethane-methanol (200:2). This chromatography gave two yellow bands. The first band was collected and evaporated to give the less polar isomer (11.3 mg), 6-chloro-3-methoxy-5,11-diaza-benzo[c]fluoren-7-one (Example 14c-1) as a yellow powder. The second band was collected and evaporated to give the more polar isomer (20.3 mg), 6-chloro-3-methoxy-5,8-diaza-benzo[c]fluoren-7-one (Example 14c-2) as a yellow powder.

Workup

  1. temperaturerefluxed for three hours
  2. customExcess phosphorus oxychloride was evaporated under reduced pressure
  3. additionThe residue was treated with water and saturated sodium hydrogen carbonate
  4. customOrange 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

Sources & evidence

ORD record
ord-0616a744050d4969abf69303612acec2
Source dataset
uspto-grants-2004_01
Patent number
US06680326B2

Reaction notes

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