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

HRID 1584041Notes

Reaction equation

HRID 1584041 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-one

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A mixute 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 by evaporation under reduced pressure. The evaporation residue, and the precipitate collected previously were dissolved in 130 ml of acetic acid and cautiously treated with 15 ml of water, while stirring. The dark red title compound is collected, washed with water, and dried to 11.5 g (95%), mp 262-264 degrees.

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 by evaporation under reduced pressure
  7. customThe evaporation residue, and the precipitate collected previously
  8. dissolutionwere dissolved in 130 ml of acetic acid
  9. additioncautiously treated with 15 ml of water
  10. customThe dark red title compound is collected
  11. washwashed with water
  12. customdried to 11.5 g (95%), mp 262-264 degrees

Sources & evidence

ORD record
ord-a779f3d954b24897bbc6a66faedc2fd6
Source dataset
uspto-grants-1985_11
Patent number
US04555572

Reaction notes

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