Hydrochloric Acid → Benzoic acid, 3-(acetylamino)-2-nitro-, ethyl ester

HRID 1276887Notes

Reaction equation

HRID 1276887 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[C:7]([N+:17]([O-:19])=[O:18])=[C:8]([CH:14]=[CH:15][CH:16]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10].Cl>CN(C)C1C=CC=CC=1>[C:1]([NH:5][C:6]1[C:7]([N+:17]([O-:19])=[O:18])=[C:8]([CH:14]=[CH:15][CH:16]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 18315537Ethyl 3-amino-2-nitrobenzoate

Product 1

HCID 18315582Benzoic acid, 3-(acetylamino)-2-nitro-, ethyl ester

Reagents, catalysts & solvents 1

HCID 949N,N-DimethylanilineSolvent

Procedure

Acetyl chloride (13 ml) was added dropwise to a solution of 2.98 g of ethyl 3-amino-2-nitrobenzoate and 20 ml of N,N-dimethylaniline in an ice bath. The mixture was stirred at room temperature for 48 hours. The reaction solution was acidified with 10% hydrochloric acid, and was extracted twice with ethyl acetate. The organic layer was washed three times with water. The solvent was distilled off under reduced pressure, and the resulting residue was crystallized with hexane. The crystals were separated through filtration, washed with hexane, and dried to give 3.30 g of ethyl 3-acetylamino-2-nitrobenzoate.

Workup

  1. extractionwas extracted twice with ethyl acetate
  2. washThe organic layer was washed three times with water
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe resulting residue was crystallized with hexane
  5. customThe crystals were separated through filtration
  6. washwashed with hexane
  7. customdried

Sources & evidence

ORD record
ord-6e003abc9eed4e3f9be2b2a64d666ae6
Source dataset
uspto-grants-2000_12
Patent number
US06166219

Reaction notes

Loading…