4-Aminobenzoic Acid → 4-(2-Chlorobenzamido)benzoic acid

HRID 1951597Notes

Reaction equation

HRID 1951597 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[Cl:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15].C(N(CC)CC)C>C(#N)C>[Cl:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)=[O:15]

Participants

5

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 8471TriethylamineHCID 691102-Chlorobenzoyl chloride

Product 1

HCID 11329884-(2-Chlorobenzamido)benzoic acidYield 54.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

under an N2 atmosphere, 4-aminobenzoic acid (2.50 g, 18.2 mmol) was dissolved in acetonitrile (100 ml) and treated with 2-chlorobenzoyl chloride (2.43 ml, 19.1 mmol). Triethylamine (2.66 ml, 19.1 mmol) was added and the reaction was allowed to stir at room temperature for four hours. The reaction was concentrated in vacuo, and the resulting solid was partitioned between Et2O and 0.5N NaOH. The layers were separated and the organic layer was discarded. The aqueous layer was acidified to pH 2 with HCl and the aqueous layer was extracted with ethyl acetate. The organic layer was dried Na2SO4, filtered and concentrated in vacuo. The resulting solid was triturated with Et2O, and the solid was collected by filtration to afford 4-(2-chlorobenzamido)benzoic acid (2.72 g, 54.2% yield). ESI m/z=276.1 (M+H+).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe resulting solid was partitioned between Et2O and 0.5N NaOH
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting solid was triturated with Et2O
  8. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-f7828a428a6740bfaeb3b3fecd1c9803
Source dataset
uspto-grants-2013_03
Patent number
US08404722B2

Reaction notes

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