Pyridine → tert-butyl 3-bromo-5-[(E)-hydroxyiminomethyl]benzoate

HRID 1257528Notes

Reaction equation

HRID 1257528 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([CH:15]=O)[CH:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].Cl.[NH2:18][OH:19].N1C=CC=CC=1>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13](/[CH:15]=[N:18]/[OH:19])[CH:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 443297Hydroxyamine hydrochloride2×HCID 58095966Tert-butyl 3-bromo-5-formylbenzoate

Product 1

HCID 58096166tert-butyl 3-bromo-5-[(E)-hydroxyiminomethyl]benzoate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 3-bromo-5-formylbenzoate (440 mg, 1.54 mmol) in dioxane (7 mL) were added hydroxylamine hydrochloride (107 mg, 1.54 mmol) and pyridine (0.13 mL, 1.54 mol). The reaction mixture was stirred at ambient temperature. After 72 h, additional hydroxylamine hydrochloride (29 mg, 0.29 mmol) and pyridine (25 μL, 0.31 mol) were added. The mixture was stirred at ambient temperature. Ater 3 h, the mixture was concentrated. Saturated aqueous NaHCO3 was added the mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated (470 mg). MS 243 (M-ten-butyl).

Workup

  1. stirringThe mixture was stirred at ambient temperature
  2. concentrationAter 3 h, the mixture was concentrated
  3. additionSaturated aqueous NaHCO3 was added the mixture
  4. extractionwas extracted with ethyl acetate (3×)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated (470 mg)

Sources & evidence

ORD record
ord-74bac171247e42b3a7bceb834a49bda4
Source dataset
uspto-grants-2013_06
Patent number
US08461185B2

Reaction notes

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