2-Bromobenzoic acid → HCID 22269765, compound

HRID 488522Notes

Reaction equation

HRID 488522 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][C:13]2[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([OH:25])=[O:24].CC([O-])=O.[K+]>CC(O)C.CC([O-])=O.CC([O-])=O.[Cu+2]>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([NH:17][C:21]3[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=3[C:23]([OH:25])=[O:24])=[CH:18][CH:19]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 69402-Bromobenzoic acidHCID 517044Potassium AcetateHCID 22269688HCID 22269688, compound

Product 1

HCID 22269765HCID 22269765, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 3776IsopropanolSolvent

Procedure

To a slurry of 4-[3-(4-nitrophenyl)propyl]aniline (4.08 g, 15.9 mmol) and 2-bromobenzoic acid (3.52 g, 17.5 mmol) in i-PrOH (100 mL) was added Cu(OAc)2 (87 mg, 0.478 mmol) and KOAc (3.44 g, 35.0 mmol) at room temperature. The resulting mixture was allowed to heat under reflux for 23 hours, then cooled to room temperature. After removing the solvent under reduced pressure, the residue was diluted with water (100 mL) and basified with aqueous 1.0 M-NaOH solution to pH 9.0. The aqueous layer was washed with Et2O (20 ml, twice) and acidified with aqueous 1.0 M-HCl solution to pH 3.0. The precipitate formed was filtered by suction and dried at 60° C. in vacuo, affording the title compound as a beige solid (5.75 g, 96% yield). mp 150-153° C. MS (Fab): 376 (MH+).

Workup

  1. temperatureto heat
  2. temperatureunder reflux for 23 hours
  3. customAfter removing the solvent under reduced pressure
  4. additionthe residue was diluted with water (100 mL)
  5. washThe aqueous layer was washed with Et2O (20 ml
  6. customThe precipitate formed
  7. filtrationwas filtered by suction
  8. customdried at 60° C. in vacuo

Sources & evidence

ORD record
ord-816a5490733e49a0ac78fa0773210e43
Source dataset
uspto-grants-2005_12
Patent number
US06972287B1

Reaction notes

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