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Methyl 3-(4-carboxy-2-nitrophenyl)propionate → 2-Oxo-1,2,3,4-tetrahydroquinoline-7-carboxylic acid

HRID 2225320
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2225320
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12](OC)=[O:13])=[C:6]([N+:16]([O-])=O)[CH:5]=1)([OH:3])=[O:2].CO.[OH-].[Na+]>[Pd].CO>[C:1]([C:4]1[CH:5]=[C:6]2[C:7]([CH2:10][CH2:11][C:12](=[O:13])[NH:16]2)=[CH:8][CH:9]=1)([OH:3])=[O:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 13242991Methyl 3-(4-carboxy-2-nitrophenyl)propionateHCID 23721981Sodium hydroxide methanol

Produkt 1

HCID 132430012-Oxo-1,2,3,4-tetrahydroquinoline-7-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

5 Grams of methyl 3-(4-carboxy-2nitrophenyl)propionate, 8.87 ml of 2.226N-sodium hydroxide methanol solution, 100 ml of methanol and 1 g of 5%-Pd-C (50% in water) were well mixed together and this mixture was catalytically reduced at a normal temperature under a normal pressure. Then the catalyst was removed from the reaction mixture by filtration, and the pH of the filtrate was adjusted to about pH=1 by adding concentrated hydrochloric acid. The precipitated crystals were collected by filtration and recrystallized from methanol to obtain 3.62 g of 7-carboxy-3,4-dihydrocarbostyril in the form of colorless needle-like crystals.

Aufarbeitung

  1. customThen the catalyst was removed from the reaction mixture by filtration
  2. additionby adding concentrated hydrochloric acid
  3. filtrationThe precipitated crystals were collected by filtration
  4. customrecrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-1017fb0b0be842cb8c69617f8751f694
Quelldatensatz
uspto-grants-1994_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
USRE034722

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