Hydroxyamine hydrochloride → HCID 136341637, compound

HRID 1964251Notes

Reaction equation

HRID 1964251 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([C:15](=O)[CH3:16])[CH:9]=2)[CH2:7][CH2:6]1)=[O:4].Cl.[NH2:19][OH:20].C([O-])(=O)C.[Na+]>CCO>[CH3:1][O:2][C:3]([C:5]1([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([C:15](=[N:19][OH:20])[CH3:16])[CH:9]=2)[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 59129379HCID 59129379, compound

Product 1

HCID 136341637HCID 136341637, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 1-(3-acetyl-4-hydroxy-phenyl)-cyclopropanecarboxylic methyl ester (14.6 g, 58.8 mmol) in EtOH (500 mL) were added hydroxylamine hydrochloride (9.00 g, 129 mmol) and sodium acetate (11.6 g, 141 mmol) at room temperature. The resulting mixture was heated at reflux overnight. After removal of EtOH under vacuum, water (200 mL) and EtOAc (200 mL) were added. The organic layer was separated and the aqueous layer was extracted with EtOAc (100 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum to give 1-[4-hydroxy-3-(1-hydroxyimino-ethyl)-phenyl]-cyclopropanecarboxylic methyl ester (14.5 g, 98%), which was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz) δ 11.09 (s, 1 H), 7.39 (d, J=2.0 Hz, 1 H), 7.23 (d, J=2.0 Hz, 1 H), 7.14 (s, 1 H), 6.91 (d, J=8.4 Hz, 1 H), 3.63 (s, 3 H), 2.36 (s, 3 H), 1.62-1.59 (m, 2 H), 1.18-1.15 (m, 2 H).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux overnight
  3. customAfter removal of EtOH under vacuum, water (200 mL) and EtOAc (200 mL)
  4. additionwere added
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with EtOAc (100 mL×3)
  7. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  8. customevaporated under vacuum

Sources & evidence

ORD record
ord-923d5a2a167e495fa7c021025dc49527
Source dataset
uspto-grants-2013_04
Patent number
US08415387B2

Reaction notes

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