Hydrochloric Acid → HCID 67164698, compound

HRID 553000Notes

Reaction equation

HRID 553000 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:26])[C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[C@@H:7]([CH3:27])[CH2:6]1)=[O:4].[OH-].[Li+].CO.Cl>O1CCCC1.O>[CH3:27][CH:7]1[CH2:6][CH:5]([C:3]([OH:4])=[O:2])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]1[C:15](=[O:26])[C:16]1[CH:17]=[CH:18][C:19]([C:22]([F:24])([F:23])[F:25])=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 58732852HCID 58732852, compound

Product 1

HCID 67164698HCID 67164698, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A round bottom flask with magnetic stirrer was charged with cis-2-methyl-1-(4-trifluoromethyl-benzoyl)-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid methyl ester (980 mg, 2.60 mmol) in tetrahydrofuran (10.0 mL). To the reaction was added a solution of lithium hydroxide (179 mg, 7.47 mmol) in water (10 mL), followed by methanol (10 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 to yield 2-methyl-1-(4-trifluoromethyl-benzoyl)-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid (mixture of cis and trans isomers) as an off-white solid (912 mg, 97%). The mixture was used without purification in subsequent reactions.

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

Sources & evidence

ORD record
ord-cbf0e69dd67c430d8e21eef1f72a954a
Source dataset
uspto-grants-2011_05
Patent number
US07951950B2

Reaction notes

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