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

HRID 74106Notes

Reaction equation

HRID 74106 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-45e4d776e6274e9fa82ebe818e850aa4
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

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