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

HRID 1801285Notes

Reaction equation

HRID 1801285 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7](/[CH:8]=[N:9]/[C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:22](=[O:26])[CH:23]([CH3:25])[CH3:24]>O1CCCC1.FC(F)(F)S([O-])(=O)=O.[Y+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>[OH:26][CH:22]1[C:19]2[C:10](=[CH:11][CH:12]=[C:13]([C:14]([O:16][CH3:17])=[O:15])[CH:18]=2)[NH:9][CH:8]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:21][CH:20]=2)[C:23]1([CH3:25])[CH3:24]

Participants

5

Reactant 2

HCID 6561IsobutyraldehydeHCID 178498134HCID 178498134, compound

Product 1

HCID 67443026Methyl 4-hydroxy-3,3-dimethyl-2-(4-nitrophenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylateYield 20%

Reagents, catalysts & solvents 2

HCID 2733939Yttrium trifluoromethanesulfonateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)-methyl 4-(4-nitrobenzylideneamino)benzoate (284 mg 1 mmol) and yttrium(III) trifluoromethanesulfonate (62 mg, 0.1 mmol) in tetrahydrofuran (5 mL) was added isobutyraldehyde (72 mg, 1.5 mmol). The resultant mixture was stirred at room temperature for 16 h. Thin layer chromatography showed the starting material was completely consumed. The reaction mixture was quenched with water and separated. The aqueous solution was extracted with dichloromethane and the combined organic layers were dried over anhydrous sodium sulfate. Solvent was removed in vacuo to give the crude product, which was purified by column chromatography (petroleum ether/ethyl acetate=3:1) to afford 70 mg of methyl 4-hydroxy-3,3-dimethyl-2-(4-nitrophenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate as a yellow solid. Yield: 20%.

Workup

  1. customwas completely consumed
  2. customThe reaction mixture was quenched with water
  3. customseparated
  4. extractionThe aqueous solution was extracted with dichloromethane
  5. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  6. customSolvent was removed in vacuo
  7. customto give the crude product, which
  8. customwas purified by column chromatography (petroleum ether/ethyl acetate=3:1)

Sources & evidence

ORD record
ord-1f2ae1c9a0d443a3b3ed7f64cf9c4c43
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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