HCID 11437128, Verbindung → 6-Benzyl-5,6,7,8-tetrahydro-1,6-naphthyridin-3-amine

HRID 1066766Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1066766
[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[N:14]=[CH:13][C:12]([N+:18]([O-])=O)=[CH:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.Cl>[NH2:18][C:12]1[CH:13]=[N:14][C:15]2[CH2:16][CH2:17][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9][C:10]=2[CH:11]=1

Komponenten

4

Edukt 1

HCID 11437128HCID 11437128, Verbindung

Produkt 1

HCID 108792166-Benzyl-5,6,7,8-tetrahydro-1,6-naphthyridin-3-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

6-Benzyl-3-nitro-5,6,7,8-tetrahydro-[1,6]-naphthyridine (790 mg; 2.93 mmol) was dissolved in ethanol (100 ml), the solution heated at 50° C. and treated with a solution of stannous chloride dihydrate (2.65 g; 11.73 mmol) in conc. hydrochloric acid (10 ml). After 10 min, the reaction mixture was concentrated under reduced pressure, neutralised by addition of 2M aqueous sodium hydroxide and extracted with DCM. The extracts were combined, washed with water, saturated brine, dried (MgSO4) and evaporated to dryness in vacuo. The brown residue was dissolved in methanol and SiO2 added. The volatiles were removed under reduced pressure and the dried SiO2 placed on the top of a silica column and subjected to chromatography, eluting with ethanol in ethyl acetate (020%) ethanol gradient. The title compound was obtained as a white powder (275 mg; 39%).

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionneutralised by addition of 2M aqueous sodium hydroxide
  3. extractionextracted with DCM
  4. washwashed with water, saturated brine
  5. dry with materialdried (MgSO4)
  6. customevaporated to dryness in vacuo
  7. dissolutionThe brown residue was dissolved in methanol
  8. additionSiO2 added
  9. customThe volatiles were removed under reduced pressure
  10. washeluting with ethanol in ethyl acetate (020%) ethanol gradient

Quellen und Nachweise

ORD-Eintrag
ord-0e9d610a75704f7c9f34675c253b6d69
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06245778B1

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