Pyridine → 1-hydroxyimino-3-phenyl-6-(3-phenyl-propoxy)-1H-indene-2-carbonitrile

HRID 19558

Reaction equation

HRID 19558 reaction equation
O=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][CH2:12][CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:9]=2)[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:3]1[C:27]#[N:28].Cl.[NH2:30][OH:31].N1C=CC=CC=1>C(O)C>[OH:31][N:30]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][CH2:12][CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:9]=2)[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:3]1[C:27]#[N:28]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 686950891-oxo-3-phenyl-6-(3-phenylpropoxy)-1H-indene-2-carbonitrile

Product 1

HCID 866140311-hydroxyimino-3-phenyl-6-(3-phenyl-propoxy)-1H-indene-2-carbonitrileYield 75.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Oxo-3-phenyl-6-(3-phenyl-propoxy)-1H-indene-2-carbonitrile (293 mg, 0.80 mmol) obtained in Example 11 was dissolved in ethanol (20 mL), and hydroxylamine hydrochloride (167 mg, 2.41 mmol) and pyridine (254 mg, 3.21 mmol) were added thereto, refluxed for 3 hrs, and cooled to RT. The resulting mixture washed with saturated sodium bicarbonate, 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 230 mg of 1-hydroxyimino-3-phenyl-6-(3-phenyl-propoxy)-1H-indene-2-carbonitrile (yield: 75%). Subsequently, 1-hydroxyimino-3-phenyl-6-(3-phenyl-propoxy)-1H-indene-2-carbonitrile (230 mg, 0.60 mmol) thus obtained was dissolved in methanol (20 mL), and 10%-palladium (230 mg) was added thereto. The mixture was stirred for 15 hrs at RT while providing H2 gas thereto using a balloon, filtered through celite, and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 90 mg of the titled compound (yield: 41%).

Workup

  1. temperaturerefluxed for 3 hrs
  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-0e82e75908e64cf49e6af380e1135d25
Source dataset
uspto-grants-2010_06
Patent number
US07745439B2

Linked notes

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