Hydrochloric Acid → 1-(4-Methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid

HRID 553003Notes

Reaction equation

HRID 553003 reaction equation
C[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:15](=[O:24])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C@@H:7]([CH3:25])[CH2:6]1)=[O:4].[OH-].[Li+].CO.Cl>O1CCCC1.O>[CH3:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([C:15]([N:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:5]([C:3]([OH:4])=[O:2])[CH2:6][CH:7]2[CH3:25])=[O:24])=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 58732829cis-1-(4-Methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid methyl ester

Product 1

HCID 671658371-(4-Methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A round bottom flask with magnetic stirrer was charged with cis-1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid methyl ester (3.00 g, 8.8 mmol) in anhydrous tetrahydrofuran (70 mL). To the reaction was added a solution of lithium hydroxide (423 mg, 18 mmol) in water (24 mL), followed by methanol (24 mL). The reaction was stirred at room temperature for 18-20 hours under an argon atmosphere. The reaction was transferred to a separatory funnel and the pH adjusted to 2 via addition of 1N hydrochloric acid. The mixture was extracted with ethyl acetate (3×35 mL) and the combined extractions were washed with brine (1×50 mL), dried over magnesium sulfate, and filtered. The filtrate was concentrated in vacuo and diethyl ether (50 mL) added to the resulting residue. The precipitated solid was collected via suction filtration to afford 1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid as a mixture of cis and trans-isomers (2.71 g, 95%). 1H-NMR (d6-DMSO) δ: 1.22 (d, 3H), 1.63 (ddd, 1H), 2.94 (ddd, 1H), 3.76 (s, 3H), 3.89 (dd, 1H), 4.83-4.91 (m, 1H), 6.51 (d, 1H), 6.72-6.76 (m, 2H), 6.95 (ddd, 1H), 7.11 (ddd, 1H), 7.26-7.35 (m, 3H). MS m/z=326 (M+1).

Workup

  1. customThe reaction was transferred to a separatory funnel
  2. extractionThe mixture was extracted with ethyl acetate (3×35 mL)
  3. extractionthe combined extractions
  4. washwere washed with brine (1×50 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo and diethyl ether (50 mL)
  8. additionadded to the resulting residue
  9. filtrationThe precipitated solid was collected via suction filtration

Sources & evidence

ORD record
ord-f051d86bb4754be9878617af9119b824
Source dataset
uspto-grants-2011_05
Patent number
US07951950B2

Reaction notes

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