4-Chloro-1,2-dinitrobenzene → HCID 22922588, compound

HRID 1081475Notes

Reaction equation

HRID 1081475 reaction equation
Cl.[NH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[C:15]([N+]([O-])=O)[CH:14]=1.CC[O-].[Na+].[Na]>CCO>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[C:15]([NH:2][CH:3]2[CH2:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4]2)[CH:14]=1

Participants

6

Reactant 4

HCID 330974-Chloro-1,2-dinitrobenzeneHCID 1227642-Aminoindan hydrochlorideHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 22922588HCID 22922588, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

26 g of 2-aminoindane hydrochloride and then 20 g of 4-chloro-1,2-dinitrobenzene are added to a solution of sodium ethylate, prepared from 0.61 g of sodium and 200 ml of EtOH, and the mixture is stirred for 48 hours at RT. The solvent is evaporated off under vacuum, the residue is extracted with AcOEt, washed with water and dried over Na2SO4 and the solvent is evaporated off under vacuum to give 10.3 g of the expected product after crystallization from EtOH. M.p.=108° C.

Workup

  1. customThe solvent is evaporated off under vacuum
  2. extractionthe residue is extracted with AcOEt
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-6f9fc53531dd4efebcd4a66b0883ab8f
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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