1-Chloro-2,6-dinitrobenzene → 2-((2,6-Dinitrophenyl)amino)benzyl alcohol

HRID 1459667Notes

Reaction equation

HRID 1459667 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[NH2:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH2:17][OH:18]>C(N(CC)CC)C>[N+:11]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[NH:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH2:17][OH:18])([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 118141-Chloro-2,6-dinitrobenzeneHCID 214392-Aminobenzyl alcohol

Product 1

HCID 540886182-((2,6-Dinitrophenyl)amino)benzyl alcoholYield 54.3%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

2.85 g (14 mmol) of 1-chloro-2,6-dinitrobenzene and 1.73 g (14 mmol) of 2-aminobenzyl alcohol were dissolved in 30 ml of triethylamine and heated under reflux for 24 hours. After concentrating, the residue was purified by silica gel column chromatography. Thus 2.2 g of 2-((2,6-dinitrophenyl)amino)benzyl alcohol was obtained. 0.29 g (1 mmol) of this powder was dissolved in 20 ml of dry dimethylformamide. After adding 40 mg (1 mmol) of sodium hydride (in oil, content: 60%), the reaction mixture was stirred at room temperature for 15 minutes and then at 150° C. for 2 hours. After cooling, 200 ml of ethyl acetate was added thereto and the mixture was washed with water, dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography. Thus 0.14 g of the title compound was obtained.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 24 hours
  3. concentrationAfter concentrating
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a600b0fd6d1b4f1baf2714706129b4bd
Source dataset
uspto-grants-1998_12
Patent number
US05854274

Reaction notes

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