Hydrochloric Acid → Ethyl 4-chloro-3-nitrobenzoate

HRID 1817204Notes

Reaction equation

HRID 1817204 reaction equation
C(=O)([O-])[O-].[K+].[K+].[N+:7]([C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[Cl:19])[C:13]([OH:15])=[O:14])([O-:9])=[O:8].[CH2:20](I)[CH3:21].Cl>CN(C=O)C>[Cl:19][C:18]1[CH:17]=[CH:16][C:12]([C:13]([O:15][CH2:20][CH3:21])=[O:14])=[CH:11][C:10]=1[N+:7]([O-:9])=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 73204-Chloro-3-nitrobenzoic acidHCID 11430Potassium Carbonate

Product 1

HCID 1268247Ethyl 4-chloro-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

To potassium carbonate (103 g) was added DMF (1 L), and a solution of 3-nitro-4-chlorobenzoic acid (125 g) in DMF (500 ml) was added thereto under ice-cooling. Ethyl iodide (116 g) was added thereto and the resulting mixture was stirred at 60° C. for 3 hours. The reaction solution was added to a 1N aqueous hydrochloric acid solution and the crystals precipitated were collected by filtration, washed with a 1N aqueous hydrochloric acid solution and water and then dried under reduced pressure to obtain ethyl 4-chloro-3-nitrobenzoate quantitatively.

Workup

  1. temperatureunder ice-cooling
  2. customthe crystals precipitated
  3. filtrationwere collected by filtration
  4. washwashed with a 1N aqueous hydrochloric acid solution and water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-1ed4eb6938304d8aa03d0ce3bfae52fe
Source dataset
uspto-grants-2009_10
Patent number
US07598240B2

Reaction notes

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