Potassium Carbonate → 8-Bromo-1,2,3,4-tetrahydronapthyridine

HRID 1861683Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1861683
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][N:9]=2)[CH2:4][CH2:3][CH2:2]1.[Br:11]N1C(=O)CCC1=O.C([O-])([O-])=O.[K+].[K+]>C(O)(=O)C>[Br:11][N:9]1[C:10]2[NH:1][CH2:2][CH2:3][CH2:4][C:5]=2[CH:6]=[CH:7][CH2:8]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 130473671,2,3,4-Tetrahydro-1,8-naphthyridine

Produkt 1

HCID 865841748-Bromo-1,2,3,4-tetrahydronapthyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 0.6730 g (5.02 mmol) 32 in 20 mL glacial acetic acid was added 1.0701 g (6.01 mmol) N-bromosuccinimide. After 16 h at 65° C., the reaction mixture was cooled to room temperature and poured onto 50 mL ice water. This was brought to pH 11 with K2CO3 and extracted with 4×100 mL CHCl3. The combined CHCl3 extracts were washed with 100 mL brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (50×115 mm silica gel, linear gradient 2-5% (10% NH4H:MeOH):CH2Cl2) yielded 33. 1H NMR (CDCl3, 400 MHz) δ 8.175 (s, 1H, ArH); 7.877 (s, 1H, ArH); 3.458-3.423 (m, 2H, CH2); 2.725 (t, 2H, J=6.26 Hz, CH2); 1.970-1.911 (m, 2H, CH2); MS (Electrospray): m/z 212.9, 214.8 (M+H, 79Br, 81Br).

Aufarbeitung

  1. extractionextracted with 4×100 mL CHCl3
  2. washThe combined CHCl3 extracts were washed with 100 mL brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (50×115 mm silica gel, linear gradient 2-5% (10% NH4H:MeOH):CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-f0057b796b874921a888db3bf6e4eb38
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06534510B2

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