Hydrochloric Acid → Ethyl 3-acetylamino-4-nitrobenzoate

HRID 276013Notes

Reaction equation

HRID 276013 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[C:9]([O:11][CH2:12][CH3:13])=[O:10].Cl>CN(C)C1C=CC=CC=1>[C:1]([NH:5][C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[C:9]([O:11][CH2:12][CH3:13])=[O:10])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 13170941Ethyl 3-amino-4-nitrobenzoate

Product 1

HCID 18315393Ethyl 3-acetylamino-4-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 949N,N-DimethylanilineSolvent

Procedure

Nine milliliters of acetyl chloride were added to a mixture of 18.4 g of ethyl 3-amino-4-nitrobenzoate and 200 ml of N,N-dimethylaniline while being cooled with ice. The mixture was stirred at room temperature for 2 hours and then at 50° C. for 2 hours. The reaction solution was poured into cold 1-N hydrochloric acid, and the mixture 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 then 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 19.6 g of ethyl 3-acetylamino-4-nitrobenzoate.

Workup

  1. temperaturewhile being cooled with ice
  2. waitat 50° C. for 2 hours
  3. extractionthe mixture 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 then 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-8a879ed2c7c3447b83a7b9dfba752853
Source dataset
uspto-grants-2002_03
Patent number
US06352985B1

Reaction notes

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