N,N-Dimethylaniline → 1-Chloro-7-[(4-methoxyphenyl)methoxy]-2,4-dinitro-9(10H)-acridinone

HRID 1584057Notes

Reaction equation

HRID 1584057 reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([N+:14]([O-:16])=[O:15])=[C:7]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)=[CH:20][CH:19]=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:19]3[C:18](=[CH:23][CH:22]=[C:21]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=4)[CH:20]=3)[NH:17][C:7]=2[C:8]([N+:14]([O-:16])=[O:15])=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 13588350HCID 13588350, compound

Product 1

HCID 135883391-Chloro-7-[(4-methoxyphenyl)methoxy]-2,4-dinitro-9(10H)-acridinone

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred, ice-cold mixture of 2.67 g of 2-chloro-6-[[4-[(4-methoxyphenyl)methoxy]phenyl]amino]-3,5-dinitrobenzoic acid, 18 ml of 1,2-dichloroethane, and 4.4 ml of N,N-dimethylaniline, was added 0.70 ml of phosphorus oxychloride. After 2.5 hours, the ice bath was removed and the mixture stirred 24 hours at room temperature. The precipitate was collected, washed with water, then with methanol, and dried to provide the title compound, melting above 240° C. with decomposition.

Workup

  1. customthe ice bath was removed
  2. customThe precipitate was collected
  3. washwashed with water
  4. dry with materialwith methanol, and dried

Sources & evidence

ORD record
ord-d4115c0ebded45208f7e8f02547d527c
Source dataset
uspto-grants-1985_11
Patent number
US04555572

Reaction notes

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