Hydrochloric Acid → HCID 66675741, Verbindung

HRID 2377094

Reaktionsgleichung

Reaktionsgleichung von HRID 2377094
[CH2:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[C:3](=[O:10])[NH:2]1.Cl.O1CCOCC1>O=[Pt]=O.CC(O)=O>[CH2:1]1[CH:9]2[CH:4]([CH2:5][NH:6][CH2:7][CH2:8]2)[C:3](=[O:10])[NH:2]1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 205051661,2-Dihydro-3H-pyrrolo(3,4-c)pyridin-3-one

Produkt 1

HCID 66675741HCID 66675741, VerbindungAusbeute 138,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 345198Adams' catalystKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

1,2-dihydro-3H-pyrrolo[3,4-c]pyridine-3-one (19.6 g, 0.146 mol) was placed into a hydrogenation reactor together with 250 mL AcOH and 1 g of PtO2 (Colonial Metals). An H2 pressure of 60 PSI was applied and the mixture hydrogenated until a pressure of 26 PSI was measured. The reaction mixture was filtered and the solvent evaporated. At the end of the evaporation, 4 N HCl in 1,4-dioxane (50 mL, 0.2 mol) was added. The solvent was evaporated to dryness. Ether (800 mL) was added and the mixture was stirred and filtered. The filter, a white solid, was dried to give 28.3 g of the desired product. 1H NMR (300 MHz, d6-DMSO) δ=9.42 (br s, 1H), 8.33 (br s, 1H), 7.88 (s, 1H), 3.44-3.25 (m, overlaps with water peak, observed integral of 6H includes water), 3.11-3.01 (m, 2H), 2.88-2.76 (m, 2H), 2.64 (br t, 1H), 2.55-2.45 (m, 3H) 1.90-1.75 (m, 1H), 1.61-1.42 (m, 1H). LCMS: 1.0 min, M+H=144.1 u/e.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent evaporated
  3. additionwas added
  4. customThe solvent was evaporated to dryness
  5. additionEther (800 mL) was added
  6. filtrationfiltered
  7. customThe filter, a white solid, was dried

Quellen und Nachweise

ORD-Eintrag
ord-254d064c0ab44d64b0d0d69eecedf2e6
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07468375B2

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