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

HRID 1257526Notes

Reaction equation

HRID 1257526 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 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 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

Conditions

Temperature
68 °C

Procedure

To a solution of tert-butyl 3-bromo-5-formylbenzoate (119 g, 417 mmol) in dioxane (2.4 L) were added hydroxylamine hydrochloride (44.0 g, 633 mmol) and pyridine (103 mL, 1.27 mol). The reaction mixture was heated to 68° C. After 16 h, the mixture was concentrated. Saturated aqueous amonium chloride was added the mixture was extracted with dichloromethane (3×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated (125.0 g). MS 243 (M-tert-butyl).

Workup

  1. concentrationthe mixture was concentrated
  2. additionSaturated aqueous amonium chloride was added the mixture
  3. extractionwas extracted with dichloromethane (3×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated (125.0 g)

Sources & evidence

ORD record
ord-cf7ad118e908404e8bac483fe30a10c1
Source dataset
uspto-grants-2013_06
Patent number
US08461185B2

Reaction notes

Loading…