Phosphorus oxychloride → HCID 86634098, compound

HRID 2275512Notes

Reaction equation

HRID 2275512 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]2[C:17]([CH:18]=1)=[N:16][C:15]1[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:9]=2[NH2:19])(=[O:3])[CH3:2].P(Cl)(Cl)(Cl)=O>>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]2[C:17]([CH:18]=1)=[N:16][C:15]1[C:10](=[CH:11][CH:12]=[C:13]([NH:4][C:1](=[O:3])[CH3:2])[CH:14]=1)[C:9]=2[NH2:19])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 57859220HCID 57859220, compound

Product 1

HCID 86634098HCID 86634098, compoundYield 175.2%

Conditions

Temperature
140 °C

Procedure

4′-Bromodiphenylamine-2-carboxylic acid 3 (430 mg, 1.47 mmol) and phosphorus oxychloride (5 mL) were charged to a 25 mL rbf equipped with a reflux condenser and nitrogen bubbler. The reaction mixture was refluxed at 140° C. for 1 hour until a red colour was obtained. The excess POCl3 was removed in vacuo. The reaction mixture was carefully quenched with ice, basified with concentrated aqueous ammonia solution (the flask was kept cold with an ice bath), and extracted with chloroform. The combined organic layers were dried over magnesium sulphate, filtered and concentrated to yield the crude product. Purification by dry chromatography using a gradient elution (Hexane e Hexane:EtOAc 96:4) afforded pure 3-bromo-9-chloroacridine 4 as a cream solid (397 mg, 92%). Analyses by 1H NMR and LCMS conformed to structure.

Workup

  1. customrbf equipped with a reflux condenser
  2. customwas obtained
  3. customThe excess POCl3 was removed in vacuo
  4. customThe reaction mixture was carefully quenched with ice
  5. customwas kept cold with an ice bath
  6. extraction), and extracted with chloroform
  7. dry with materialThe combined organic layers were dried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto yield the crude product
  11. customPurification
  12. customby dry chromatography
  13. washa gradient elution (Hexane e Hexane:EtOAc 96:4)

Sources & evidence

ORD record
ord-b9a8d54be0ac4c8b95c7ca5b666445ae
Source dataset
uspto-grants-2015_09
Patent number
US09127164B2

Reaction notes

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