Hydrochloric Acid → ethyl 3-[N-(2-chlorobenzyl)acetylamino]-4-nitrobenzoate

HRID 276014Notes

Reaction equation

HRID 276014 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17])[C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:3])[CH3:2].[H-].[Na+].[Cl:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH2:24]Br.Cl>CN(C)C=O>[Cl:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH2:24][CH2:2][C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11905alpha-Bromo-o-chlorotolueneHCID 24758Sodium hydrideHCID 18315393Ethyl 3-acetylamino-4-nitrobenzoate

Product 1

HCID 18315549ethyl 3-[N-(2-chlorobenzyl)acetylamino]-4-nitrobenzoateYield 81.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1.706 g of ethyl 3-acetylamino-4-nitrobenzoate in 12 ml of N,N-dimethylformamide were added 0.406 g of 60% sodium hydride while being cooled with ice, and the mixture was stirred at room temperature for 40 minutes. A solution of 1.806 g of 2-chlorobenzyl bromide in 10 ml of N,N-dimethylformamide was added thereto, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into cold 1-N hydrochloric acid, and the mixed solution was extracted twice with ethyl acetate. The organic layer was washed with 1-N hydrochloric acid and then with water, and was dried. The solvent was distilled off under reduced pressure. The residue was purified through silica-gel column chromatography (eluent: a mixture of ethyl acetate and hexane at a ratio of from 1:10 to 1:4) to give 2.08 g of oily ethyl 3-[N-(2-chlorobenzyl)acetylamino]-4-nitrobenzoate.

Workup

  1. temperaturewhile being cooled with ice
  2. stirringthe mixture was stirred at room temperature for 3 hours
  3. extractionthe mixed solution was extracted twice with ethyl acetate
  4. washThe organic layer was washed with 1-N hydrochloric acid
  5. dry with materialwith water, and was dried
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe residue was purified through silica-gel column chromatography (eluent
  8. additiona mixture of ethyl acetate and hexane at a ratio of from 1:10 to 1:4)

Sources & evidence

ORD record
ord-86bbd89d855f442c8e9f95991ba4ccc3
Source dataset
uspto-grants-2002_03
Patent number
US06352985B1

Reaction notes

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