Sodium Hydroxide → 4-Methyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylic acid

HRID 1710450Notizen

Reaktionsgleichung

C([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[CH:10]=[C:11]3[C:18](=[O:19])[NH:17][CH2:16][CH:15]([CH3:20])[N:12]3[C:13]=2[CH:14]=1)=[O:5])C.[OH-].[Na+]>C1COCC1.CCO>[CH3:20][CH:15]1[N:12]2[C:13]3[CH:14]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[CH:8][C:9]=3[CH:10]=[C:11]2[C:18](=[O:19])[NH:17][CH2:16]1

Komponenten

Reaktionsbedingungen

Temperatur: 75 °C

Versuchsvorschrift

To a suspension of ethyl ester from step d above (3.2 g, 11.75 mmol) in 100 mL of THF/EtOH (1:1 v/v) was added 1 N aq NaOH (43 mL, 43 mmol). The reaction mixture became a clear solution upon addition of 1 N NaOH. The clear solution was heated at 75° C. for 2 h. The reaction was concentrated and the crude residue was dissolved in water, and extracted with ether. The aqueous layer was acidified to pH ˜4 with 3 N HCl (˜16 mL). A large amount of white precipitate formed which was filtered off and rinsed with cold ether. The wet product was dried in the vacum oven (50° C.) to provide 2.2 g of 4-Methyl-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-7-carboxylic acid, yield 77% for two steps.

Aufarbeitung

concentrationThe reaction was concentrated
dissolutionthe crude residue was dissolved in water
extractionextracted with ether
customA large amount of white precipitate formed which
filtrationwas filtered off
washrinsed with cold ether
customThe wet product was dried in the vacum oven (50° C.)

Quellen und Nachweise

ORD-Eintrag: ord-74332686b88e4961841adb7d2eaed21a
Quelldatensatz: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07790712B2

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