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

HRID 840944Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 840944
[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): δ12.35 (s, 1H); 8.12 (m, 1H); 7.90 (m, 1H); 7.14 (m, 1H); 5.75 (s, 2H). Electrospray MS m/a 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-4d8b20ecc7b5463899929013c55b8eb4
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06369086B1

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