Benzene → HCID 57892427, compound

HRID 1821089Notes

Reaction equation

HRID 1821089 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]([NH:16][CH2:17][CH2:18][CH2:19][NH2:20])=[C:11]1[C:6]([CH2:7][CH2:8][CH2:9][CH2:10]1)=[N:5]2.[NH:21]1[C:30]2[CH2:29][CH2:28][CH2:27][C:26](=O)[C:25]=2[CH:24]=[CH:23][C:22]1=[O:32].C1C=CC=CC=1>C(O)(=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]([NH:16][CH2:17][CH2:18][CH2:19][NH:20][CH:26]1[CH2:27][CH2:28][CH2:29][C:30]3[NH:21][C:22](=[O:32])[CH:23]=[CH:24][C:25]1=3)=[C:11]1[C:6]([CH2:7][CH2:8][CH2:9][CH2:10]1)=[N:5]2

Participants

6

Reactant 3

HCID 241BenzeneHCID 2674502-Hydroxy-7,8-dihydro-5(6H)-quinolinoneHCID 23645224N-(3-aminopropyl)-6-chloro-1,2,3,4-tetrahydroacridin-9-amine

Product 1

HCID 57892427HCID 57892427, compoundYield 58.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 962WaterSolvent

Procedure

To a flask was added N1-(6-chloro-1,2,3,4-tetrahydro-acridin-9-yl)-propane-1,3-diamine (116 mg, 0.40 mmoL), 7,8-dihydro-1H,6H-quinoline-2,5-dione (85 mg, 0.52 mmoL), benzene (4 mL) and one drop of acetic acid, and the resulting mixture as heated to reflux under nitrogen. The water generated from the reaction was removed by Dean-Stark apparatus. After refluxing for 24 h, the benzene was distilled off and methanol (2 mL) was added, followed by sodium borohydride (30 mg, 0.80 mmoL). After stiring at room temperature for 24 h, the reaction was stopped and concentrated. The mixture was treated with saturated sodium bicarbonate and methylene chloride. The layers were separated and the aqueous layer was extracted with methylene chloride twice. The combined methylene chloride extract was combined, dried over sodium sulfate, filtered and concentrated. The resulting residue was purified by preparative TLC using 15% MeOH/1% ammonium hydroxide in methylene chloride to give the desired product (102 mg, 0.23 mmoL, 58%).

Workup

  1. temperaturethe resulting mixture as heated
  2. temperatureto reflux under nitrogen
  3. customwas removed by Dean-Stark apparatus
  4. temperatureAfter refluxing for 24 h
  5. distillationthe benzene was distilled off
  6. additionmethanol (2 mL) was added
  7. concentrationconcentrated
  8. additionThe mixture was treated with saturated sodium bicarbonate and methylene chloride
  9. customThe layers were separated
  10. extractionthe aqueous layer was extracted with methylene chloride twice
  11. extractionThe combined methylene chloride extract
  12. dry with materialdried over sodium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated
  15. customThe resulting residue was purified by preparative TLC

Sources & evidence

ORD record
ord-2a70bd9ca21d478594900edca2411e5c
Source dataset
uspto-grants-2009_10
Patent number
US07605265B2

Reaction notes

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