p-Anisoyl chloride → cis-1-(4-Methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid methyl ester

HRID 553002Notes

Reaction equation

HRID 553002 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C@@H:7]([CH3:15])[CH2:6]1)=[O:4].C(N(CC)C(C)C)(C)C.[C:25](Cl)(=[O:34])[C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1.C(=O)(O)[O-].[Na+]>ClCCl.C(OCC)C>[CH3:1][O:2][C:3]([C@H:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:25](=[O:34])[C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[C@@H:7]([CH3:15])[CH2:6]1)=[O:4]

Participants

7

Reactant 4

HCID 7477p-Anisoyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 50853311rac-methyl (2R,4S)-2-methyl-1,2,3,4-tetrahydroquinoline-4-carboxylate

Product 1

HCID 58732829cis-1-(4-Methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid methyl esterYield 78.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A round bottom flask with magnetic stirrer was charged with cis-2-methyl-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid methyl ester (5.42 g, 26 mmol) in dichloromethane (100 mL) under an argon atmosphere at room temperature. To the reaction was added N,N-diisopropylethylamine (11.8 mL, 68 mmol), followed by p-anisoyl chloride (6.31 g, 37 mmol). The reaction was stirred at room temperature for 18-20 hours and poured into saturated sodium bicarbonate (1000 mL), diluted with dichloromethane (50 mL), and shaken vigorously. The resulting organic layer was separated, washed with brine (1×100 mL), dried over magnesium sulfate, and filtered. The filtrate was concentrated in vacuo to afford an oily residue. Diethyl ether (50 mL) was added to the residue and the resulting white solid was collected via suction filtration to afford cis-1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid methyl ester (6.94 g, 78%).

Workup

  1. stirringshaken vigorously
  2. customThe resulting organic layer was separated
  3. washwashed with brine (1×100 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customto afford an oily residue
  8. filtrationthe resulting white solid was collected via suction filtration

Sources & evidence

ORD record
ord-28d99f28542c4a64bae2f8616287ffb9
Source dataset
uspto-grants-2011_05
Patent number
US07951950B2

Reaction notes

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