Hydrochloric Acid → 1,3-Dihydro-2H-pyrrolo[3,2-b]pyridin-2-one

HRID 1168235Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1168235
[NH2:1][C:2]1[C:3]([CH2:8][C:9]([O:11]CC)=O)=[N:4][CH:5]=[CH:6][CH:7]=1.Cl>C(OCC)C>[NH:1]1[C:2]2[C:3](=[N:4][CH:5]=[CH:6][CH:7]=2)[CH2:8][C:9]1=[O:11]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 15475339Ethyl 2-(3-aminopyridin-2-yl)acetate

Produkt 1

HCID 3163671,3-Dihydro-2H-pyrrolo[3,2-b]pyridin-2-oneAusbeute 78,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Ethyl 2-(3-amino-pyridin-2-yl)-acetate (6.94 g, 0.038 mol) was dissolved in diethyl ether (100 mL) at room temperature. Hydrochloric acid (2M, 35 mL) was added, and the reaction was stirred for 30 minutes. The volatiles were removed to afford a brown solid that was recrystallized from ethanol and diethyl ether to provide the title compound (4.0 g, 62% yield). 1H NMR 400 MHz (DMSO-d6): δ 12.35 (s, 1H); 8.12 (m, 1H); 7.90 (m, 1H); 7.14 (m, 1H); 5.75 (s, 2H). Electrospray MS m/z 135 (M+H).

Aufarbeitung

  1. customThe volatiles were removed
  2. customto afford a brown solid that
  3. customwas recrystallized from ethanol and diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-622837f737a64eb09b02c9713636e05f
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06624171B1

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