Phosphorus oxychloride → 1,9-Dichloro-7-methoxy-4-nitroacridine

HRID 280253Notes

Reaction equation

HRID 280253 reaction equation
[Cl:1][C:2]1[C:7]([C:8](O)=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:25])=O>ClC1C=CC=CC=1>[Cl:1][C:2]1[C:7]2[C:6](=[N:11][C:12]3[C:17]([C:8]=2[Cl:25])=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[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 135883541,9-Dichloro-7-methoxy-4-nitroacridine

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A stirred mixture of 12.9 of 6-chloro-2[(4-methoxyphenyl)amino]-3-nitrobenzoic acid, 25 ml of chlorobenzene and 50 ml of phosphorus oxychloride is heated to reflux temperature over a period of one hour, and held under reflux for 4.5 hours. The mixture is allowed to cool, the precipitate collected, providing the yellow title compound, mp 243-246 degrees after recrystallization from toluene.

Workup

  1. temperatureis heated
  2. temperatureto reflux temperature over a period of one hour
  3. temperatureunder reflux for 4.5 hours
  4. temperatureto cool
  5. customthe precipitate collected

Sources & evidence

ORD record
ord-6cfa0e4f8ded4377afde1258066fbcbb
Source dataset
uspto-grants-1986_05
Patent number
US04588730

Reaction notes

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