2-Chloro-4-nitrobenzoic acid → HCID 966782, compound

HRID 2233268Notes

Reaction equation

HRID 2233268 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[C:17]#[N:18]>S(Cl)(Cl)=O>[C:17]([C:16]1[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=1[NH:14][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:2]=1[Cl:1])#[N:18]

Participants

4

Reactant 2

HCID 74482-Chloro-4-nitrobenzoic acidHCID 729132-Aminobenzonitrile

Product 1

HCID 966782HCID 966782, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 2-chloro-4-nitrobenzoic acid (6.00 g, 29.8 mmol) in thionyl chloride (20 ml) was heated at reflux for 2.5 hours. The reaction was cooled, the excess thionyl chloride was evaporated in vacuo and the residue was azeotroped with toluene (2×25 ml). The residue was taken up in toluene (35 ml), 2-aminobenzonitrile (1.75 g, 14.8 mmol) was added and the reaction heated at reflux for 2 hours. The reaction was cooled, the solvent was removed in vacuo and the residue was absorbed onto silica gel. Purification by flash chromatography on silica gel, eluting with dichloromethane, yielded N-(2-cyanophenyl)-2-chloro-4-nitrobenzamide (1.30 g, 27% yield) as a pale yellow solid:

Workup

  1. temperatureat reflux for 2.5 hours
  2. temperatureThe reaction was cooled
  3. customthe excess thionyl chloride was evaporated in vacuo
  4. customthe residue was azeotroped with toluene (2×25 ml)
  5. temperaturethe reaction heated
  6. temperatureat reflux for 2 hours
  7. temperatureThe reaction was cooled
  8. customthe solvent was removed in vacuo
  9. customthe residue was absorbed onto silica gel
  10. customPurification by flash chromatography on silica gel
  11. washeluting with dichloromethane

Sources & evidence

ORD record
ord-0e6b7a69e7d347fc8c33f18ca82d5180
Source dataset
uspto-grants-2010_05
Patent number
US07709479B1

Reaction notes

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