Sodium Hydroxide → HCID 68352333, compound

HRID 2174565Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:18])=[C:7](C(OCC)=O)[C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[N:24]([CH3:28])[CH:23]=[CH:22]2.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:18])=[CH:7][C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[N:24]([CH3:28])[CH:23]=[CH:22]2

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of ethyl 7-chloro-4-hydroxy-6-(1-methyl-1H-indol-5-yl)-2-oxo-1,2-dihydro-3-quinolinecarboxylate (Example 27) (50 mg, 0.126 mmol) in ethanol (5 mL) was added sodium hydroxide 1N (0.315 mL, 0.315 mmol). The reaction mixture was stirred at 80° C. for 2 h. Additional solution of 1N sodium hydroxide was added (1 mL) and the reaction mixture was stirred at 160° C. for another 30 nm under microwave irradiation. After cooling, the solvent was evaporated and the mixture was dissolved in water and acidified with 1N HCl. The resulting solid was filtered, dried then triturated in hot acetonitrile, filtered and dried to give the title compound 7-chloro-4-hydroxy-6-(1-methyl-1H-indol-5-yl)quinolin-2(1H)-one (16 mg, 0.049 mmol, 39.1% yield) as a cream solid. LCMS: (M+H)+=325; Rt=2.66 min. HRMS: calculated for C18H14ClN2O2 (M+H)+: 325.0744. found: 325.0739.

Workup

stirringthe reaction mixture was stirred at 160° C. for another 30 nm under microwave irradiation
temperatureAfter cooling
customthe solvent was evaporated
dissolutionthe mixture was dissolved in water
filtrationThe resulting solid was filtered
customdried
customthen triturated in hot acetonitrile
filtrationfiltered
customdried

Sources & evidence

ORD record: ord-9df59e5af994415d9f57181ea7ad91b8
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09061998B2

Reaction notes

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