Hydrochloric Acid → HCID 67166315, compound

HRID 553010Notes

Reaction equation

HRID 553010 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]([C:17]2[CH:18]=[N:19][C:20](Cl)=[CH:21][CH:22]=2)=[O:16])[C@@H:7]([CH3:24])[CH2:6]1)=[O:4].[CH3:25][O-:26].[Na+].CO.Cl>COCCOC>[CH3:25][O:26][C:20]1[N:19]=[CH:18][C:17]([C:15]([N:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:5]([C:3]([OH:2])=[O:4])[CH2:6][CH:7]2[CH3:24])=[O:16])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10942334Sodium MethoxideHCID 86608601HCID 86608601, compound

Product 1

HCID 67166315HCID 67166315, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of cis-1-(6-chloro-pyridine-3-carbonyl)-2-methyl-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid methyl ester (620 mg, 1.8 mmol) in ethylene glycol dimethyl ether (6.00 mL) was added at 0° C. a 5M solution of sodium methoxide in methanol (3.3 mL, 16.2 mmol). The reaction mixture was stirred at room temperature for 20 hours. The reaction mixture was acidified to pH 1 by addition of aqueous 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated in vacuo to yield 1-(6-methoxy-pyridine-3-carbonyl)-2-methyl-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid (190 mg, 32%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d61505477c0245dc90b4c220682eefb5
Source dataset
uspto-grants-2011_05
Patent number
US07951950B2

Reaction notes

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