Hydrochloric Acid → HCID 57691175, compound

HRID 40290Notes

Reaction equation

HRID 40290 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([C:13]([CH3:19])([CH3:18])[C:14]([O:16]C)=[O:15])=[CH:8][CH:7]=2.[Li+].[OH-].CO.Cl>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([C:13]([CH3:19])([CH3:18])[C:14]([OH:16])=[O:15])=[CH:8][CH:7]=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 57691013Methyl 2-(3-methoxyquinolin-6-yl)-2-methylpropanoate

Product 1

HCID 57691175HCID 57691175, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-(3-methoxyquinolin-6-yl)-2-methylpropanoate (400 mg, 1543 μmol), LiOH (1928 μl, 7713 μmol) [4M], MeOH (2 mL), and THF (2 mL) was stirred at 50° C. overnight. LCMS suggests full conversion. Solution cooled, acidified to pH 1 with 5M HCl, and precipitate collected by filtration. White cake washed with water (2 mL) and EtOH (1 mL). Product air dried for 3 h and isolated as a white solid. MS (ESI pos. ion) m/z: 246 (MH+). Calc'd exact mass for C14H15NO3: 245.

Workup

  1. temperatureSolution cooled
  2. filtrationcollected by filtration
  3. washWhite cake washed with water (2 mL) and EtOH (1 mL)
  4. customProduct air dried for 3 h
  5. customisolated as a white solid

Sources & evidence

ORD record
ord-c20ff44461e84547888811a9a83f0f65
Source dataset
uspto-grants-2013_09
Patent number
US08524900B2

Reaction notes

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