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

HRID 1805092Notes

Reaction equation

HRID 1805092 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-9b19997709d54bb29058c4f98df98d02
Source dataset
uspto-grants-2013_01
Patent number
US08354427B2

Reaction notes

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