5-Chloro-2-nitrobenzoic acid → Methyl 5-chloro-2-nitrobenzoate

HRID 1094980Notes

Reaction equation

HRID 1094980 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH2:14](OC(C1C(N)SC2=CC=CC=12)=O)C.S(Cl)(Cl)=O>CO>[CH3:14][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 172865-Chloro-2-nitrobenzoic acidHCID 24386Thionyl ChlorideHCID 53438117HCID 53438117, compound

Product 1

HCID 171018Methyl 5-chloro-2-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Chloro-2-nitro-benzoic acid (compound A′) (5.0 g) was dissolved in methanol (150 ml). Thionyl chloride (9.5 ml) was added to the solution at 0° C., and the mixture was heated under reflux with stirring for 15 hr. After the completion of the reaction, distilled water was added thereto at 0° C., and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with distilled water and saturated brine, was dried over sodium sulfate, and was then concentrated to give 5-chloro-2-nitro-benzoic acid methyl ester as a useful intermediate (12.9 g, yield 92%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. customAfter the completion of the reaction
  4. distillationdistilled water
  5. additionwas added
  6. extractionat 0° C., and the mixture was subjected to separatory extraction with chloroform
  7. washThe organic layer was washed with distilled water and saturated brine
  8. dry with materialwas dried over sodium sulfate
  9. concentrationwas then concentrated

Sources & evidence

ORD record
ord-29454db4aea84064b37d4fc79f9d02ed
Source dataset
uspto-grants-2012_03
Patent number
US08134015B2

Reaction notes

Loading…