Sodium Hydroxide → N-Indolin-6-yl-4-oxo-1H-quinoline-3-carboxamide

HRID 401439Notes

Reaction equation

HRID 401439 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:13][C:14]([C:16]3[C:25](=[O:26])[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[NH:18][CH:17]=3)=[O:15])[CH:11]=2)[CH2:6][CH2:5]1)(=O)C.[OH-].[Na+]>C(O)C>[NH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:13][C:14]([C:16]3[C:25](=[O:26])[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[NH:18][CH:17]=3)=[O:15])[CH:11]=2)[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57567377HCID 57567377, compound

Product 1

HCID 57567409N-Indolin-6-yl-4-oxo-1H-quinoline-3-carboxamideYield 27.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-(1-acetylindolin-6-yl)-4-oxo-1H-quinoline-3-carboxamide (233) (43 mg, 0.12 mmol), 1N NaOH solution (0.5 mL) and ethanol (0.5 mL) was heated to reflux for 48 h. The solution was concentrated and the residue was dissolved in DMSO (1 mL) and purified by HPLC (10-99% CH3CN—H2O) to yield the product, N-indolin-6-yl-4-oxo-1H-quinoline-3-carboxamide (258) (10 mg, 20%). HPLC ret. time 2.05 min, 10-99% CH3CN, 5 min run; ESI-MS 306.3 m/z (MH+).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 48 h
  3. concentrationThe solution was concentrated
  4. dissolutionthe residue was dissolved in DMSO (1 mL)
  5. custompurified by HPLC (10-99% CH3CN—H2O)

Sources & evidence

ORD record
ord-6a192281436a4084b0ebca0633297dc7
Source dataset
uspto-grants-2014_06
Patent number
US08741925B2

Reaction notes

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