Hydrochloric Acid → HCID 86755953, compound

HRID 369127Notes

Reaction equation

HRID 369127 reaction equation
[CH:1]([C:3]1[CH:17]=[CH:16][CH:15]=[CH:14][C:4]=1[CH:5]([C:8]1[O:12][N:11]=[C:10]([CH3:13])[CH:9]=1)[O:6][CH3:7])=O.Cl.[NH2:19][OH:20].N1C=CC=CC=1.Cl>CO>[OH:20][N:19]=[CH:1][C:3]1[CH:17]=[CH:16][CH:15]=[CH:14][C:4]=1[CH:5]([C:8]1[O:12][N:11]=[C:10]([CH3:13])[CH:9]=1)[O:6][CH3:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 18332473HCID 18332473, compound

Product 1

HCID 86755953HCID 86755953, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 1.39 g (6 mmol) of 5-(2-formyl-α-methoxybenzyl)-3-methylisoxazole in 12 ml of methanol was added 0.83 g (12 mmol) of hydroxylamine hydrochloride and 1.07 ml (13.2 mmol) of pyridine and stirred under reflux for 2 hours. After completion of the reaction, 200 ml of 0.1 N hydrochloric acid was added and extracted twice with 100 ml of dichloromethane. The dichloromethane layer was dried over anhydrous magnesium and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate/n-hexane) to give 5-(2-hydroxyiminomethyl-α-methoxybenzyl)-3-methylisoxazole (1.20 g, 81.2%) as oil.

Workup

  1. temperatureunder reflux for 2 hours
  2. additionwas added
  3. extractionextracted twice with 100 ml of dichloromethane
  4. dry with materialThe dichloromethane layer was dried over anhydrous magnesium
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-898e57c588204652be62b278e63cdb3a
Source dataset
uspto-grants-2000_10
Patent number
US06136837

Reaction notes

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