2-Nitrobenzoic acid → 2-Nitrobenzoyl chloride

HRID 1681686Notes

Reaction equation

HRID 1681686 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6](O)=[O:7])([O-:3])=[O:2].S(Cl)([Cl:15])=O>>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([Cl:15])=[O:7])([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 110872-Nitrobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 118752-Nitrobenzoyl chloride

Procedure

A mixture of 2-nitrobenzoic acid (5 g) and thionyl chloride (5 ml) was heated under reflux for 30 minutes and then concentrated in vacuo. The residue was dissolved in dry toluene (20 ml) and the volatile material was evaporated. This procedure was repeated. The 2-nitrobenzoyl chloride thus obtained was dissolved in methylene chloride (20 ml). This solution was then added to a solution of 3-(aminomethyl)pyridine (3.24 g) and triethylamine (3.03 g) in methylene chloride (50 ml) at 0° C. After the addition was complete, the reaction mixture was washed with water, dried (MgSO4) and evaporated to give 3-(N-(2-nitrobenzoyl)aminomethyl)pyridine as a solid of satisfactory purity and in essentially quantitative yield.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in dry toluene (20 ml)
  5. customthe volatile material was evaporated

Sources & evidence

ORD record
ord-65c93bc525854eeaa770661aa5a40cca
Source dataset
uspto-grants-1992_12
Patent number
US05173496

Reaction notes

Loading…