HCID 178498133, compound → Methyl 2-(3-chloro-5-nitrophenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

HRID 1801326Notes

Reaction equation

HRID 1801326 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([N+:20]([O-:22])=[O:21])[CH:19]=1)/[CH:5]=[N:6]/[C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1>O1CCCC1.FC(F)(F)S([O-])(=O)=O.[Y+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]2[C:10]([CH3:15])([CH3:9])[CH:11]([OH:12])[C:8]3[C:7](=[CH:16][CH:15]=[C:10]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=3)[NH:6]2)[CH:17]=[C:18]([N+:20]([O-:22])=[O:21])[CH:19]=1

Participants

4

Reactant 1

HCID 178498133HCID 178498133, compound

Product 1

HCID 67442943Methyl 2-(3-chloro-5-nitrophenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylateYield 117.4%

Reagents, catalysts & solvents 2

HCID 2733939Yttrium trifluoromethanesulfonateCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (E)-methyl 4-(3-chloro-5-nitrobenzylideneamino)benzoate (346 mg, 1.09 mmol) in dry tetrahydrofuran (4 mL) was added yttrium(III) trifluoromethanesulfonate (34 mg, 0.054 mmol). The mixture was stirred under a nitrogen atmosphere. Then a solution of isobutyl aldehyde (95 mg, 1.30 mmol) in tetrahydrofuran (1 mL) was added via syringe. The mixture was stirred overnight. The reaction mixture was purified by column chromatography (petroleum ether: ethyl acetate=10:1) to afford 250 mg of methyl 2-(3-chloro-5-nitrophenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate as a crude product. (Yield=59%). MS (ESI+APCI) M+1-water=373.

Workup

  1. stirringThe mixture was stirred overnight
  2. customThe reaction mixture was purified by column chromatography (petroleum ether: ethyl acetate=10:1)

Sources & evidence

ORD record
ord-7f0d715f85934be3a18121960d0cd8af
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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