Water → HCID 67442640, compound

HRID 1801029Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:22])[C:5]1[CH:10]=[CH:9][C:8]([N:11]=[CH:12][C:13]2[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([Br:21])[CH:14]=2)=[CH:7][CH:6]=1)[CH3:2].[CH:23](=[O:27])[CH:24]([CH3:26])[CH3:25].O>O1CCCC1.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>[CH2:1]([O:3][C:4]([C:5]1[CH:10]=[C:9]2[C:8](=[CH:7][CH:6]=1)[NH:11][CH:12]([C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([Br:21])[CH:14]=1)[C:24]([CH3:26])([CH3:25])[CH:23]2[OH:27])=[O:22])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

To a mixture of 4-{[1-(3-bromo-5-methoxy-phenyl)-methylidene]-amino}-benzoic acid ethyl ester (4.5 g, 12.4 mmol) and ytterbium(III) triflate hydrate (0.77 g, 1.24 mmol) in dry tetrahydrofuran (20 mL) at 25° C. was added isobutyraldehyde (0.89 g, 12.4 mmol) and water (0.22 mL, 12.4 mmol) dropwise. The reaction mixture was stirred at 25° C. for 5 h. Then the reaction mixture was concentrated in vacuo and the residue was extracted with ethyl acetate (2×100 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 2-(3-bromo-5-methoxy-phenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (5.4 g, 100%) as a light yellow oil: LC/MS m/e calcd for C21H24BrNO4 M+: 434.3, observed: 418.1.

Workup

concentrationThen the reaction mixture was concentrated in vacuo
extractionthe residue was extracted with ethyl acetate (2×100 mL)
washwashed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-9a924b30862c480e9a29d01cf7259633
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08344137B2

Reaction notes

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