Water → Methyl 2-(4-fluoro-3-nitrophenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

HRID 1801292Notes

Reaction equation

HRID 1801292 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5](/[CH:6]=[N:7]/[C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[N+:20]([O-:22])=[O:21].[CH:23](=[O:27])[CH:24]([CH3:26])[CH3:25].O>O1CCCC1.FC(F)(F)S([O-])(=O)=O.[Y+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH:6]2[C:24]([CH3:26])([CH3:25])[CH:23]([OH:27])[C:17]3[C:8](=[CH:9][CH:10]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[CH:16]=3)[NH:7]2)=[CH:4][C:3]=1[N+:20]([O-:22])=[O:21]

Participants

6

Reactant 3

HCID 962WaterHCID 6561IsobutyraldehydeHCID 178498131HCID 178498131, compound

Product 1

HCID 67442290Methyl 2-(4-fluoro-3-nitrophenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylateYield 70.1%

Reagents, catalysts & solvents 2

HCID 2733939Yttrium trifluoromethanesulfonateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (E)-methyl 4-(4-fluoro-3-nitrobenzylideneamino)benzoate (3.62 g, 12.0 mmol) in tetrahydrofuran (24 mL), yttrium(III) trifluoromethanesulfonate (75 mg, 0.12 mmol) and isobutyraldehyde (0.87 g, 12.0 mmol) were added under nitrogen at room temperature The resultant mixture was stirred at room temperature for 20 hours (turned into clear in 10 min). Water was added to the reaction mixture and extracted with Ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate. Solvent was removed and the residue was purified by column (petroleum ether/ethyl acetate=3:1, silica gel) to afford methyl 2-(4-fluoro-3-nitrophenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate 3.15 g (70%) as a yellow solid.

Workup

  1. extractionextracted with Ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customSolvent was removed
  5. customthe residue was purified by column (petroleum ether/ethyl acetate=3:1, silica gel)

Sources & evidence

ORD record
ord-55705165bde74acd9302818dc229ba18
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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