Dichloromethane → (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic Acid Hydrochloride

HRID 633960Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 633960
[OH-].[Na+].CN1CC[C:7]2([CH2:18][C:17]3[C:12](=[N:13][CH:14]=[C:15](/[CH:19]=[CH:20]/[C:21]([O:23]CC)=[O:22])[CH:16]=3)[NH:11][C:10]2=[O:26])CC1.[Cl:27]CCl>C(O)C>[ClH:27].[O:26]=[C:10]1[NH:11][C:12]2[N:13]=[CH:14][C:15](/[CH:19]=[CH:20]/[C:21]([OH:23])=[O:22])=[CH:16][C:17]=2[CH2:18][CH2:7]1

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 68338070HCID 68338070, Verbindung

Produkt 1

HCID 66905305(E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic Acid Hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

An aqueous solution of sodium hydroxide (1N, 7.83 mL) was added to a solution of (E)-ethyl 3-(1′-methyl-2-oxo-2,4-dihydro-1H-spiro[[1,8]naphthyridine-3,4′-piperidine]-6-yl)acrylate (860 mg, 2.61 mmol) in a mixture of dichloromethane (10 mL) and ethanol (10 mL) at room temperature. The reaction mixture was stirred at 45° C. overnight then concentrated to dryness. The residue was acidified by addition of an aqueous solution of hydrochloric acid (1N, 30 mL) until pH 1. The resulting solid was filtered and washed with water and diethyl ether. The title product was obtained as a white solid (586 mg, 66%).

Aufarbeitung

  1. concentrationthen concentrated to dryness
  2. additionThe residue was acidified by addition of an aqueous solution of hydrochloric acid (1N, 30 mL) until pH 1
  3. filtrationThe resulting solid was filtered
  4. washwashed with water and diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-ab0fd4c108c04deeb7755bd23dcd823b
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321769B2

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