Cyclohexanone → 6,9-Dichloro-1,2,3,4-tetrahydroacridine

HRID 1821085Notes

Reaction equation

HRID 1821085 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=O.[C:12]1(=O)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.P(Cl)(Cl)([Cl:21])=O>>[Cl:11][C:9]1[CH:10]=[C:2]2[C:3](=[CH:7][CH:8]=1)[C:4]([Cl:21])=[C:17]1[C:12]([CH2:13][CH2:14][CH2:15][CH2:16]1)=[N:1]2

Participants

4

Reactant 3

HCID 7967CyclohexanoneHCID 24813Phosphorus oxychlorideHCID 666462-Amino-4-chlorobenzoic acid

Product 1

HCID 2196646,9-Dichloro-1,2,3,4-tetrahydroacridineYield 98.2%

Procedure

To a mixture of 2-amino-4-chlorobenzoic acid (4.5 g, 26.23 mmol) and cyclohexanone (2.72 mL, 26.23 mmoL) was added 22 mL phosphorus oxychloride. The mixture was heated to reflux for 3 hours. The excess phosphorus oxychloride was distilled off and the resulting mixture was treated with saturated sodium bicarbonate. The light brown precipitate was filtered, rinsed with water and dried under vacuum to give the desired product 6.50 g (25.77 mmoL, 98.2%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. distillationThe excess phosphorus oxychloride was distilled off
  4. additionthe resulting mixture was treated with saturated sodium bicarbonate
  5. filtrationThe light brown precipitate was filtered
  6. washrinsed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-d7a238f84fac403183eb85f47fecef7d
Source dataset
uspto-grants-2009_10
Patent number
US07605265B2

Reaction notes

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