Hydrochloric Acid → [1-phenyl-5-(phenylamino)-1H-pyrazol-3-yl]methanol

HRID 2194708Notes

Reaction equation

[C:1]1([N:7]2[C:11]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:10][C:9]([C:19](OCC)=[O:20])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1.C1(C)C=CC=CC=1>[C:1]1([N:7]2[C:11]([NH:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[CH:10][C:9]([CH2:19][OH:20])=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of ethyl 1-phenyl-5-(phenylamino)-1H-pyrazole-3-carboxylate (345 mg) in tetrahydrofuran (10 mL) was cooled to −78° C., and a 1.5 mol/L solution (3.7 mL) of diisobutylaluminum hydride in toluene was added dropwise. After stirring at 0° C. for 1 hr, the mixture was treated with 1 mol/L hydrochloric acid, and extracted with ethyl acetate. The extract was washed with 1 mol/L hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=2:1→1:2) to give the title compound as a pale-yellow oil (yield 318 mg, yield quantitative).

Workup

extractionextracted with ethyl acetate
washThe extract was washed with 1 mol/L hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate solution and saturated brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=2:1→1:2)

Sources & evidence

ORD record: ord-178ebe5f66614d05a861e3a8d840ce8d
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08334301B2

Reaction notes

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