Phosphorus oxychloride → 6,8,9-Trichloro-1,2,3,4-tetrahydroacridine

HRID 1821086Notes

Reaction equation

HRID 1821086 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[C:14]([Cl:16])[CH:15]=1)[C:12](O)=[C:11]1[C:6]([CH2:7][CH2:8][CH2:9][CH2:10]1)=[N:5]2.P(Cl)(Cl)([Cl:20])=O>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[C:14]([Cl:16])[CH:15]=1)[C:12]([Cl:20])=[C:11]1[C:6]([CH2:7][CH2:8][CH2:9][CH2:10]1)=[N:5]2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178515159HCID 178515159, compound

Product 1

HCID 551884546,8,9-Trichloro-1,2,3,4-tetrahydroacridineYield 68%

Procedure

A solution of 6,8-dichloro-1,2,3,4-tetrahydro-acridin-9-ol (18 g, 6.7 mmoL) in phosphorus oxychloride (45 mL) was heated to 135 degree Celsius for 45 min. After the excess phosphorus oxychloride was distilled under vacuum, the remaining mixture was allowed to cool to room temperature and treated with saturated sodium bicarbonate. The resulting suspension was extracted with diethyl ether (×3). The combined ether extract was washed with brine, dried with sodium sulfate, filtered and concentrated. Recrystallization from ethanol afforded the desired product (1.3 g, 68%) as a white solid.

Workup

  1. distillationAfter the excess phosphorus oxychloride was distilled under vacuum
  2. additiontreated with saturated sodium bicarbonate
  3. extractionThe resulting suspension was extracted with diethyl ether (×3)
  4. extractionThe combined ether extract
  5. washwas washed with brine
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-41ed94f0bce843aa8e3c0cd77b60d2d8
Source dataset
uspto-grants-2009_10
Patent number
US07605265B2

Reaction notes

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