Sodium Hydroxide → 2-(1-Methylcyclopropyl)quinoline-6-carboxylic acid

HRID 1094656Notes

Reaction equation

HRID 1094656 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([C:15]1([CH3:18])[CH2:17][CH2:16]1)[CH:9]=[CH:8]2)=[O:4].[OH-].[Na+]>CO>[CH3:18][C:15]1([C:10]2[CH:9]=[CH:8][C:7]3[C:12](=[CH:13][CH:14]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=3)[N:11]=2)[CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66636963Methyl 2-(1-methylcyclopropyl)quinoline-6-carboxylate

Product 1

HCID 595441812-(1-Methylcyclopropyl)quinoline-6-carboxylic acidYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl-2-(1-methylcyclopropyl)quinoline-6-carboxylate (225 mg, 0.93 mmol) and 2M sodium hydroxide solution (2 ml, 4 mmol) in methanol (10 ml) was heated at 60° C. for 2 hours. After the solvent was evaporated in vacuo, the residue was dissolved with water. The aqueous solution was neutralized with 2M hydrochloric acid solution (2 ml) and the precipitate white solid was extracted with ethyl acetate (×3). The combined solution was washed with brine, dried over sodium sulfate and concentrated in vacuo to give crude white solid, which was recrystallized from ethyl acetate and hexane to furnish the title compound (177 mg, 84%) as a white solid. MS (ESI): m/z 228.15 [M+H]+, 226.13 [M−H]−.

Workup

  1. customAfter the solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved with water
  3. extractionthe precipitate white solid was extracted with ethyl acetate (×3)
  4. washThe combined solution was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give crude white solid, which
  8. customwas recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-744c9afb6ed940a4b64ea98ec7437f18
Source dataset
uspto-grants-2012_03
Patent number
US08134004B2

Reaction notes

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