Pyridine → methyl 4-hydroxy-3-[(E)-N-hydroxy-C-propylcarbonimidoyl]benzoate

HRID 14249Notes

Reaction equation

HRID 14249 reaction equation
[C:1]([C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][C:15]=1[OH:16])[C:9]([O:11][CH3:12])=[O:10])(=O)[CH2:2][CH2:3][CH3:4].N1C=CC=CC=1.Cl.[NH2:24][OH:25]>C(O)C>[OH:16][C:15]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1/[C:1](=[N:24]/[OH:25])/[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 12533653Methyl 3-butanoyl-4-hydroxybenzoate

Product 1

HCID 136200566methyl 4-hydroxy-3-[(E)-N-hydroxy-C-propylcarbonimidoyl]benzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of methyl 3-butyryl-4-hydroxybenzoate, pyridine (3.7 mL, 46 mmol), and hydroxylamine hydrochloride (3.55 g, 51 mmol) in ethanol (30 mL) was heated reflux for 2 h. The mixture was concentrated under reduced pressure and partitioned between water and ethyl acetate. The organic layer was washed with 1 N hydrochloric acid, saturated sodium bicarbonate, dried (sodium sulfate), filtered, and concentrated under reduced pressure to afford a crude oil. Purification by flash column chromatography (silica, 10:1 hexanes/ethyl acetate) provided methyl 4-hydroxy-3-[(1E)-N-hydroxybutanimidoyl]benzoate (170 mg): 1H NMR (500 MHz, CD3OD): δ 8.30-8.28 (m, 1H), 7.85-7.82 (m, 1H), 6.92-6.89 (m, 1H), 3.88 (s, 3H), 2.87-2.84 (m, 2H), 1.67-1.60 (m, 2H), 1.05-1.00 (m, 3H).

Workup

  1. temperaturereflux for 2 h
  2. concentrationThe mixture was concentrated under reduced pressure
  3. custompartitioned between water and ethyl acetate
  4. washThe organic layer was washed with 1 N hydrochloric acid, saturated sodium bicarbonate
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto afford a crude oil
  9. customPurification by flash column chromatography (silica, 10:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-daec9b6c54014d8785b5047f78210205
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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