Pyridine → Methyl 2-(5-bromopentanoylamino)-6-chlorobenzoate

HRID 1714792Notes

Reaction equation

HRID 1714792 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].N1C=CC=CC=1.[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24](Cl)=[O:25]>O1CCCC1>[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([NH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:3]=1[C:4]([O:6][CH3:7])=[O:5])=[O:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 5211735-Bromovaleryl chlorideHCID 592849Methyl 2-amino-6-chlorobenzoate

Product 1

HCID 23155867Methyl 2-(5-bromopentanoylamino)-6-chlorobenzoateYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 750 mg of methyl 2-amino-6-chlorobenzoate as synthesized in above Step 7-18-A in 10 ml of tetrahydrofuran, first 700 mg of pyridine and then 800 mg of 5-bromovaleryl chloride were added under cooling with ice. The solution was warmed to room temperature, stirred for an hour and the solvent was distilled off under reduced pressure. The residue was extracted with ethyl acetate, washed with saturated aqueous sodium hydrogencarbonate solution, 1N hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure to provide 1.34 g (96%) of methyl 2-(5-bromopentanoylamino)-6-chlorobenzoate.

Workup

  1. temperatureunder cooling with ice
  2. distillationthe solvent was distilled off under reduced pressure
  3. extractionThe residue was extracted with ethyl acetate
  4. washwashed with saturated aqueous sodium hydrogencarbonate solution, 1N hydrochloric acid and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4a17914bc77e47a79084d6255851881a
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

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