Hydroxyamine hydrochloride → 3-Cyclopentyloxy-4-methoxybenzaldehyde oxime

HRID 1169846Notes

Reaction equation

HRID 1169846 reaction equation
Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].[CH:9]1([O:14][C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=2[O:23][CH3:24])[CH:18]=O)[CH2:13][CH2:12][CH2:11][CH2:10]1>C(O)C>[CH:9]1([O:14][C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=2[O:23][CH3:24])[CH:18]=[N:2][OH:3])[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 27358933-Cyclopentyloxy-4-methoxybenzaldehyde

Product 1

HCID 28228453-Cyclopentyloxy-4-methoxybenzaldehyde oxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroxylamine hydrochloride (0.473 g, 6.8181 mmol) and sodium acetate (0.56 g, 6.8181 mmol) was added to a stirred solution of compound of Formula II (0.5 g, 2.2727 mmol) in ethanol (8 mL). The reaction mixture was stirred at room temperature for 50 minutes. Ethanol was evaporated under reduced pressure, which was diluted with water (20 mL) and the organic compound was extracted with ethyl acetate (2×15 mL). The ethyl acetate layer was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to afford compound of Formula III. Analysis by 1H NMR spectroscopy gave the following peaks (CDCl3): 9.84 (s, 1H), 8.07 (s, 1H), 6.84-7.24 (m, 3H), 4.79-4.83 (m, 1H), 3.87 (s, 3H), 1.62-2.18 (m, 8H).

Workup

  1. customEthanol was evaporated under reduced pressure, which
  2. additionwas diluted with water (20 mL)
  3. extractionthe organic compound was extracted with ethyl acetate (2×15 mL)
  4. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0efc959d2c934d3fb1fe4e5fc08c5c2f
Source dataset
uspto-grants-2010_11
Patent number
US07825147B2

Reaction notes

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