Phosphorus oxychloride → 1-chloro-7-methoxy-4-nitro-10H-acridin-9-one

HRID 1248835Notes

Reaction equation

HRID 1248835 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=O)=[C:6]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:5]([N+:20]([O-:22])=[O:21])=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O>ClC1C=CC=CC=1>[Cl:1][C:2]1[C:7]2[C:8](=[O:10])[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=3)[NH:11][C:6]=2[C:5]([N+:20]([O-:22])=[O:21])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 27780126-Chloro-2-(4-methoxyanilino)-3-nitrobenzoic acid

Product 1

HCID 4382311-chloro-7-methoxy-4-nitro-10H-acridin-9-oneYield 95%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A mixture of 12.9 g of 6-chloro-2[(4-methoxyphenyl)amino]-3-nitrobenzoic acid, 25 ml of chlorobenzene and 50 ml of phosphorus oxychloride was stirred and heated to reflux temperature over a period of one hour, and held under reflux for 4.5 hours. The mixture was cooled, filtered, and the filtrate concentrated to a viscous dark residue in vacuo. This residue and the precipitate collected previously were dissolved in 130 ml of acetic acid and cautiously treated with 15 ml of water with stirring. The resulting dark red solid was collected, washed with water, and dried to provide 11.5 g (95%) of the title compound, mp 262°-264° C.

Workup

  1. temperatureheated
  2. temperatureto reflux temperature over a period of one hour
  3. temperatureunder reflux for 4.5 hours
  4. temperatureThe mixture was cooled
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated to a viscous dark residue in vacuo
  7. customThis residue and the precipitate collected previously
  8. dissolutionwere dissolved in 130 ml of acetic acid
  9. additioncautiously treated with 15 ml of water
  10. stirringwith stirring
  11. customThe resulting dark red solid was collected
  12. washwashed with water
  13. customdried

Sources & evidence

ORD record
ord-85c549d2ec9a4a8b902a19c227d07cf5
Source dataset
uspto-grants-1986_12
Patent number
US04626540

Reaction notes

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