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

HRID 2045605Notes

Reaction equation

HRID 2045605 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 3-chloro-5-nitrobenzaldehyde (371 mg, 0.1 mmol) in ethanol (6 mL) was added methyl 4-aminobenzoate (302 mg, 2.0 mmol). After a while, solids precipitated from the resulting clear yellow solution. The precipitated solid was filtered and 346 mg of (E)-methyl 4-(3-chloro-5-nitrobenzylideneamino)benzoate as a yellow solid was obtained. Yield=54%. 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-35cc67db828247769fedd02b02f8c41d
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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