Phosphorus oxychloride → Acridine, 1,2,3,4-tetrahydro-9-chloro-

HRID 2251098Notes

Reaction equation

HRID 2251098 reaction equation
[C:1]1(=[N:7][C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10](O)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.P(Cl)(Cl)([Cl:19])=O>C(Cl)Cl>[Cl:19][C:10]1[C:9]2[C:8]([N:7]=[C:1]3[C:6]=1[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:16][CH:15]=[CH:14][CH:13]=2

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 46156362-Cyclohexylideneamino-benzoic acid

Product 1

HCID 21495Acridine, 1,2,3,4-tetrahydro-9-chloro-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

2-Cyclohexylideneamino-benzoic acid (1.5 g, 6.9 mmol) was added to phosphorus oxychloride (4 mL) at 0° C. and stirred for 5 minutes followed by heating to 100° C. for 45 minutes. The reaction mixture was cooled to room temperature and slowly poured onto ice (˜100 g) and stirred for 30 minutes. CH2Cl2 (100 mL) was added and the mixture stirred for 5 minutes and the organic layer separated. The aq. layer was extracted with CH2Cl2 (50 mL). The combined CH2Cl2 layers were washed with sat. aq. NaHCO3 (2×50 mL), sat. aq. NaCl (50 mL), dried over Na2SO4, decanted and concentrated to give 9-chloro-1,2,3,4-tetrahydro-acridine, which, was used without further purification.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. additionslowly poured onto ice (˜100 g)
  3. stirringstirred for 30 minutes
  4. stirringthe mixture stirred for 5 minutes
  5. customthe organic layer separated
  6. extractionThe aq. layer was extracted with CH2Cl2 (50 mL)
  7. washThe combined CH2Cl2 layers were washed with sat. aq. NaHCO3 (2×50 mL), sat. aq. NaCl (50 mL)
  8. dry with materialdried over Na2SO4
  9. customdecanted
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-edc9d4358fdf4329bfb343b084922113
Source dataset
uspto-grants-2008_01
Patent number
US07319103B2

Reaction notes

Loading…