N,N-Dimethylaniline → 1-Chloro-4-nitro-7-(phenylmethoxy)-9(10H)-acridinone

HRID 1248833Notes

Reaction equation

HRID 1248833 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:17][CH:16]=2)[C:3]=1[C:4](O)=[O:5].CN(C)C1C=CC=CC=1.P(Cl)(Cl)(Cl)=O>ClCCCl>[Cl:1][C:2]1[C:3]2[C:4](=[O:5])[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH:19]=3)[NH:14][C:7]=2[C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 13588229HCID 13588229, compound

Product 1

HCID 135883221-Chloro-4-nitro-7-(phenylmethoxy)-9(10H)-acridinone

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Four grams of 2-chloro-5-nitro-6-[[4-(phenylmethoxy)phenyl]amino]benzoic acid was suspended in 80 ml of boiling 1,2-dichloroethane to which 0.2 ml of N,N-dimethylaniline was added followed by 8.0 ml of phosphorus oxychloride. The mixture was stirred under reflux for 30 minutes and cooled overnight. The resulting suspension was filtered providing the title compound as a red solid, mp 216°-217° C.

Workup

  1. additionwas added
  2. temperatureunder reflux for 30 minutes
  3. temperaturecooled overnight
  4. filtrationThe resulting suspension was filtered

Sources & evidence

ORD record
ord-e7d21bc4d78845a6a4ba72571a10a7fd
Source dataset
uspto-grants-1986_12
Patent number
US04626540

Reaction notes

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