Pyridine → 1-hydroxyimino-3-phenyl-6-(3-phenylpropoxy)-1H-indene-2-carboxylic acid ethyl ester

HRID 19551

Reaction equation

HRID 19551 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=O)[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:9]=2)=[O:5])[CH3:2].Cl.[NH2:33][OH:34].N1C=CC=CC=1>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[N:33][OH:34])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:9]=2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 118452821-oxo-3-phenyl-6-(3-phenylpropoxy)-1H-indene-2-carboxylic acid ethyl ester

Product 1

HCID 866140261-hydroxyimino-3-phenyl-6-(3-phenylpropoxy)-1H-indene-2-carboxylic acid ethyl esterYield 58.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Oxo-3-phenyl-6-(3-phenyl-propoxy)-1H-indene-2-carboxylic acid ethyl ester (1.5 g, 3.64 mmol) obtained in Example 7 was dissolved in ethanol (100 mL), hydroxylamine hydrochloride (759 mg, 10.92 mmol) and pyridine (1.15 g, 15.56 mmol) were added thereto, refluxed for 1 hr, and cooled to RT. The resulting mixture washed with saturated sodium bicarbonate and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 0.91 g of the titled compound (yield: 58%).

Workup

  1. temperaturerefluxed for 1 hr
  2. washThe resulting mixture washed with saturated sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated under a reduced pressure
  7. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-ef70888cc8144573b9748559881916f2
Source dataset
uspto-grants-2010_06
Patent number
US07745439B2

Linked notes

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