N,N-Dimethylaniline → 1,6-dichloro-7-methoxy-4-nitro-9(10H)-acridinone

HRID 280260

Reaction equation

HRID 280260 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])=[C:14]([Cl:20])[CH:13]=2)[C:5]([N+:21]([O-:23])=[O:22])=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.CN(C)C1C=CC=CC=1>ClCCCl>[Cl:1][C:2]1[C:7]2[C:8](=[O:10])[C:17]3[C:12](=[CH:13][C:14]([Cl:20])=[C:15]([O:18][CH3:19])[CH:16]=3)[NH:11][C:6]=2[C:5]([N+:21]([O-:23])=[O:22])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 135883476-Chloro-2-[(3-chloro-4-methoxyphenyl)amino]-3-nitrobenzoic acid

Product 1

HCID 135883311,6-dichloro-7-methoxy-4-nitro-9(10H)-acridinone

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 17 g of 6-chloro-2-[(3-chloro-4-methoxyphenyl)amino]-3-nitrobenzoic acid, 35 ml of phosphorus oxychloride, 1 ml of N,N-dimethylaniline and 150 ml 1,2-dichloroethane was heated under reflux for 45 minutes. The resulting solid was collected by filtration from the hot reaction mixture and was washed with chloroform to provide 1,6-dichloro-7-methoxy-4-nitro-9(10H)-acridinone, mp 284°-285° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 45 minutes
  3. filtrationThe resulting solid was collected by filtration from the hot reaction mixture
  4. washwas washed with chloroform

Sources & evidence

ORD record
ord-6deb89f2f8274ae29ed35081d8032961
Source dataset
uspto-grants-1986_05
Patent number
US04588730

Linked notes

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