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Hydrochloric Acid → 4-Fluoro-benzyl-4-hydroxy-6-methyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester

HRID 970479
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 970479
[C:1]([O:9]CC)(=O)[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[H][H].[F:16][C:17]1[CH:36]=[CH:35][C:20]([CH2:21][N:22]2[C:27]3[CH:28]=[CH:29][C:30]([CH3:32])=[CH:31][C:26]=3[C:25](=O)[O:24]C2=O)=[CH:19][CH:18]=1.Cl>CC(N(C)C)=O>[CH2:6]([O:5][C:3]([C:2]1[C:1](=[O:9])[N:22]([CH2:21][C:20]2[CH:35]=[CH:36][C:17]([F:16])=[CH:18][CH:19]=2)[C:27]2[C:26]([C:25]=1[OH:24])=[CH:31][C:30]([CH3:32])=[CH:29][CH:28]=2)=[O:4])[CH3:7]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 865946424-Fluorobenzyl-6-methyl-1H-benzo[d][1,3]oxazine-2,4-dioneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 69478041
4-Fluoro-benzyl-4-hydroxy-6-methyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester
Ausbeute 71,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Neat diethyl malonate (3.04 mL, 20 mmol) was added slowly to a suspension of sodium hydride (60% in mineral oil, 0.88 g, 22 mmol) in dimethylacetamide under N2 atmosphere. The mixture was stirred at room temperature until the evolution of hydrogen gas ceased, then the mixture was heated to 90° C. for 30 min and cooled to room temperature. A solution of Compound 13 (6.3 g, 22 mmol) in dimethylacetamide was added slowly and the mixture heated overnight at 110° C. The mixture was cooled to room temperature, poured into ice water, and acidified by cold 10% HCl. The solids formed were filtered, washed several times by water, and dried at room temperature under vacuum to yield 5.1 g (71%) of white solids. M.P. 130° C. 1H NMR (DMSO-d6): δ 1.31 (t, J=7.0 Hz, 3H), 2.34 (s, 3H), 4.37 (q, J=7.5 Hz, 2H), 5.94 (s, 2H), 7.09-7.32 (m, 5H), 7.45 (dd, J=1.6, 8.7 Hz, 1H), 7.86 (d, J=1.5 Hz, 1H). EIMS m/z 356 (M+1), 378 (M+23). Anal. (C20H18FNO4) C, H, N.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. temperaturethe mixture heated overnight at 110° C
  3. temperatureThe mixture was cooled to room temperature
  4. customThe solids formed
  5. filtrationwere filtered
  6. washwashed several times by water
  7. customdried at room temperature under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-07506196af9e4c41bb1a18f123bffd2c
Quelldatensatz
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07312220B2

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