Methanol → (3-Hydroxyimino-6-methoxy-indan-1-yl)-acetic acid methyl ester

HRID 1616649Notes

Reaction equation

HRID 1616649 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[C:7](=O)[CH2:6]1.Cl.[NH2:19][OH:20].C([O-])(=O)C.[Na+].CO>O>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[C:7](=[N:19][OH:20])[CH2:6]1

Participants

6

Reactant 4

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 15751354(6-Methoxy-3-oxo-indan-1-yl)-acetic acid methyl ester

Product 1

HCID 86650493(3-Hydroxyimino-6-methoxy-indan-1-yl)-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

(6-Methoxy-3-oxo-indan-1-yl)-acetic acid methyl ester (12.0 g), hydroxylamine hydrochloride (4.6 g), and sodium acetate (5.5 g) dissolved in water (40 mL) and methanol (50 mL) are stirred at reflux temperature for 3 h. After cooling to room temperature, water (100 mL) is added and the solution is extracted with ethyl acetate. The combined organic extracts are washed with water and brine and dried (MgSO4). The solvent is evaporated to give the product as a brown oil.

Workup

  1. temperatureat reflux temperature for 3 h
  2. extractionthe solution is extracted with ethyl acetate
  3. washThe combined organic extracts are washed with water and brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent is evaporated

Sources & evidence

ORD record
ord-a90123e7c17c4c29b3e0096b07aec653
Source dataset
uspto-grants-2014_07
Patent number
US08765780B2

Reaction notes

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