1-Chloro-2,4-Dinitrobenzene → HCID 23353533, compound

HRID 235127Notes

Reaction equation

HRID 235127 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[N+:19]([C:22]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:23]=1Cl)([O-:21])=[O:20]>CN(C=O)C>[N+:19]([C:22]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:23]=1[NH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1)([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 61-Chloro-2,4-DinitrobenzeneHCID 233534847-Amino-1-(4-methyl-1-piperazinyl)-naphthalene

Product 1

HCID 23353533HCID 23353533, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-amino-1-(4-methyl-1-piperazinyl)-naphthalene (0.05 g, 0.207 mmol) and 2,4-dinitrochlorobenzene (0.75 g, 0.373 mmol) in dry DMF (2 mL) was refluxed 2 hours. The solvent was removed in vacuo and the residue was taken up in methylene chloride. The organic phase was washed with saturated sodium bicarbonate and brine, dried over calcium sulfate and concentrated. The residue was recrystallized from ether to give 0.045g (54%) of the title compound: mp 153°-154° C. Analysis calculated for C21H21N5O4 ; C, 61.91; H, 5.20; N, 17.19. Found: C, 61.42; H, 5.10; N, 16.79.

Workup

  1. temperaturewas refluxed 2 hours
  2. customThe solvent was removed in vacuo
  3. washThe organic phase was washed with saturated sodium bicarbonate and brine
  4. dry with materialdried over calcium sulfate
  5. concentrationconcentrated
  6. customThe residue was recrystallized from ether

Sources & evidence

ORD record
ord-d350038e425f4d378a6a5db3d65178b3
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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