Water → HCID 67443627, compound

HRID 1800971Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].O.[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O.[CH:48](=[O:52])[CH:49]([CH3:51])[CH3:50].O>O1CCCC1>[CH3:1][S:2]([C:5]1[CH:10]=[C:9]2[C:8](=[CH:7][CH:6]=1)[NH:11][CH:12]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=1)[C:49]([CH3:51])([CH3:50])[CH:48]2[OH:52])(=[O:4])=[O:3]

Participants

Conditions

Temperature: 25 °C

Procedure

To a mixture of (4-methanesulfonyl-phenyl)-(3-nitro-benzylidene)-amine (10 g, 33 mmol) and ytterbium(III) triflate hydrate (2.05 g, 3.3 mmol) in dry tetrahydrofuran (100 mL) at 25° C. was added isobutyraldehyde (3.3 mL, 36.3 mmol) and water (0.6 mL, 33 mmol) dropwise. The reaction mixture was stirred at 25° C. for 16 h. Then the reaction mixture was concentrated in vacuo and the residue was extracted with ethyl acetate (2×200 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 6-methanesulfonyl-3,3-dimethyl-2-(3-nitro-phenyl)-1,2,3,4-tetrahydro-quinolin-4-ol (10 g, 92%) as a light yellow oil: LC/MS m/e calcd for C18H20N2O5S (M+H)+: 377.43, observed: 376.8.

Workup

concentrationThen the reaction mixture was concentrated in vacuo
extractionthe residue was extracted with ethyl acetate (2×200 mL)
washwashed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-53c43b327fee4b38b529630a7a3135b2
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08344137B2

Reaction notes

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