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

HRID 17890Notes

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].[OH:29][NH2:30].Cl.N1C=CC=CC=1>C(O)C>[OH:29][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

Conditions

Temperature: 70 °C

Procedure

1-Oxo-3-phenyl-6-(3-phenylpropoxy)-1H-indene-2-carbonitrile (200 mg, 0.547 mmol) was dissolved in ethanol. Hydroxy amine.hydrochloric acid (114 mg, 1.64 mmol) and pyridine (173 mg, 2.18 mmol) were added thereto and the mixture was stirred for 4 hours at 70° C. The organic layer extracted with ethyl acetate was washed with distilled water, dried over anhydrous magnesium sulfate, concentrated, and the resulting residue was purified by column chromatography (ethyl acetate:hexane=1:2) to obtain trails 1-hydroxy imino-3-phenyl-6-(3-phenylpropyloxy)-1H-indene-2-carbonitrile (95 mg, yield 45%) as a red solid,

Workup

extractionThe organic layer extracted with ethyl acetate
washwas washed with distilled water
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated
customthe resulting residue was purified by column chromatography (ethyl acetate:hexane=1:2)

Sources & evidence

ORD record: ord-aa319d98b94f435396b145547cac0460
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741323B2

Reaction notes

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