Sodium Hydroxide → HCID 66746848, compound

HRID 1467047Notes

Reaction equation

HRID 1467047 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:12][CH2:13][CH:14]([CH3:16])[CH3:15])[N:5]=[C:4]([CH3:17])[C:3]=1[C:18]([O:20]CC)=[O:19].[OH-].[Na+]>CCO>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:12][CH2:13][CH:14]([CH3:16])[CH3:15])[N:5]=[C:4]([CH3:17])[C:3]=1[C:18]([OH:20])=[O:19]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66746856HCID 66746856, compound

Product 1

HCID 66746848HCID 66746848, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-amino-5-isobutoxy-2-methylquinoline-3-carboxylate (Example 41a, 18.0 g, 59.53 mmol) in EtOH (150 mL) was added aqueous NaOH solution (3 N, 50 mL) and the reaction mixture was refluxed overnight. It was then cooled down to room temperature and the solution was filtered to remove any possible solid residue. The filtrate was carefully neutralized with 6N HCl to pH 7 at 0° C. The resultant precipitate was collected by filtration, washed with water, re-dissolved in EtOH (700 mL) and water (20 mL), and treated with activated charcoal (650 mg) at 70° C. for 0.5 h. The charcoal was removed by filtration, and the filtrate was concentrated and stored at 4° C. overnight. The resulting precipitate was collected by filtration, washed with cold H2O, and dried under vacuum at 60° C. overnight to give the title compound as a white solid (4.24 g, 26%). M.p.: 203.7° C. 1H NMR (400 MHz, DMSO-d6) δ 1.01-1.02 (m, 6H), 2.19-2.24 (m, 1H), 2.77 (s, 3H), 4.05 (d, J=6.4 Hz, 2H), 7.08 (d, J=8.0 Hz, 1H), 7.33 (d, J=8.0 Hz, 1H), 7.71 (t, J=8.0 Hz, 1H), 8.9 (brs, 1H), 11.45 (brs, 1H), 13.2 (brs, 1H). MS 275 (MH+). Elemental Analysis Calculated (Found) for C15H18N2O3.0.75H2O: C, 62.59%; (62.23%); H, 6.83%; (7.25%); N, 9.76%; (9.73%).

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. filtrationthe solution was filtered
  3. customto remove any possible solid residue
  4. customwas carefully neutralized with 6N HCl to pH 7 at 0° C
  5. filtrationThe resultant precipitate was collected by filtration
  6. washwashed with water
  7. dissolutionre-dissolved in EtOH (700 mL)
  8. additionwater (20 mL), and treated with activated charcoal (650 mg) at 70° C. for 0.5 h
  9. customThe charcoal was removed by filtration
  10. concentrationthe filtrate was concentrated
  11. filtrationThe resulting precipitate was collected by filtration
  12. washwashed with cold H2O
  13. customdried under vacuum at 60° C. overnight

Sources & evidence

ORD record
ord-58c4d8eff61b4637a713eb88b95d28d1
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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