Hydroxyamine hydrochloride → HCID 75103735, compound

HRID 42682Notes

Reaction equation

HRID 42682 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:11])=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O.[NH2:12][OH:13].Cl>C(O)C.O>[CH3:1][O:2][C:3]1[C:4]([CH3:11])=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[N:12][OH:13]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 131626633-Methoxy-2-methylbenzaldehyde

Product 1

HCID 75103735HCID 75103735, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To an ice-cooled and stirred suspension of 3-methoxy-2-methylbenzaldehyde (0.269 g, 1.8 mmol) in ethanol (15 ml) a solution of NaOAc.3H2O (1.3 eq) and NH2OH.HCl (1.3 eq) in water (5 ml) was added dropwise within 5 minutes. The resulting suspension was stirred at room temperature until the starting material was consumed (monitored by TLC). After evaporation of the ethanol in vacuo, water was added to the residue. Then the precipitated crystals were filtered off. The crude product was purified by column chromatography with a mixture of chloroform:ethyl acetate (95:5) as the eluent.

Workup

  1. additionwas added dropwise within 5 minutes
  2. stirringThe resulting suspension was stirred at room temperature until the starting material
  3. customwas consumed (monitored by TLC)
  4. customAfter evaporation of the ethanol in vacuo, water
  5. additionwas added to the residue
  6. filtrationThen the precipitated crystals were filtered off
  7. customThe crude product was purified by column chromatography with a mixture of chloroform:ethyl acetate (95:5) as the eluent

Sources & evidence

ORD record
ord-7110f1ee85b549b895d76688602304b6
Source dataset
uspto-grants-2013_09
Patent number
US08536210B2

Reaction notes

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