Sodium Hydroxide → HCID 57567285, Verbindung

HRID 470131Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 470131
C([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][C:14]=1[NH:15][C:16]([C:18]1[C:27](=[O:28])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=1)=[O:17])[NH:11][CH:10]=[CH:9]2)=[O:5])C.[OH-].[Na+]>C1COCC1>[O:28]=[C:27]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][CH:19]=[C:18]1[C:16]([NH:15][C:14]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][NH:11]2)=[CH:7][C:6]=1[C:4]([OH:5])=[O:3])=[O:17]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 575673926-[(4-oxo-1H-quinolin-3-yl)carbonylamino]-1H-indole-5-carboxylic acid ethyl ester

Produkt 1

HCID 57567285HCID 57567285, VerbindungAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A mixture of 6-[(4-oxo-1H-quinolin-3-yl)carbonylamino]-1H-indole-5-carboxylic acid ethyl ester (188) (450 mg, 1.2 mmol) and 1N NaOH solution (5 mL) in THF (10 mL) was heated at 85° C. overnight. The reaction mixture was partitioned between EtOAc and water. The aqueous layer was acidified with 1N HCl solution to pH 5, and the precipitate was filtered, washed with water and air dried to yield 6-[(4-oxo-1H-quinolin-3-yl)carbonylamino]-1H-indole-5-carboxylic acid (188-I) (386 mg, 93%). 1H-NMR (400 MHz, DMSO-d6) δ 12.92-12.75 (m, 2H), 11.33 (s, 1H), 8.84 (s, 1H), 8.71 (s, 1H), 8.30 (dd, J=8.1, 0.9 Hz, 1H), 8.22 (s, 1H), 7.80-7.72 (m, 2H), 7.49 (t, J=8.0 Hz, 1H), 7.41 (t, J=2.7 Hz, 1H), 6.51 (m, 1H); HPLC ret. time 2.95 min, 10-99% CH3CN, 5 min run; ESI-MS 376.2 m/z (MH+).

Aufarbeitung

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. filtrationthe precipitate was filtered
  3. washwashed with water and air
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-dbe06662f1ae4b4bb7f3570ab598d792
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629162B2

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