Trifluoroacetic acid → Methyl 2-(3-chloro-5-nitrophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

HRID 1801327Notes

Reaction equation

HRID 1801327 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]2[C:20]([CH3:22])([CH3:21])[CH:19](O)[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:24]([O:26][CH3:27])=[O:25])[CH:17]=3)[NH:12]2)[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]2[C:20]([CH3:21])([CH3:22])[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:24]([O:26][CH3:27])=[O:25])[CH:17]=3)[NH:12]2)[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67442943Methyl 2-(3-chloro-5-nitrophenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

Product 1

HCID 67439798Methyl 2-(3-chloro-5-nitrophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylateYield 52.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl 2-(3-chloro-5-nitrophenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (250 mg, 0.64 mmol) in dichloromethane (5 mL) was added a solution of trifluoroacetic acid (300 mg, 0.8 mmol) in dichloromethane (5 mL) under a nitrogen atmosphere with an ice bath slowly (1.5-2 h). The resultant mixture was stirred at room temperature for 3 h. The mixture was treated with 1 g of Sodium bicarbonate and filtered. The filtrate was concentrated, and purified on preparative Thin layer chromatography to afford 125 mg of methyl 2-(3-chloro-5-nitrophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate as a yellow solid. Yield=52%.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. custompurified on preparative Thin layer chromatography

Sources & evidence

ORD record
ord-1633cd33200249ef8bb07de33303d87b
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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