Ammonia → Methyl 5-(aminocarbonyl)-3-chloro-1H-pyrrole-2-carboxylate

HRID 1874967Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1874967
[NH3:1].[Cl:2][C:3]1[CH:7]=[C:6]([C:8](Cl)=[O:9])[NH:5][C:4]=1[C:11]([O:13][CH3:14])=[O:12]>C1COCC1>[NH2:1][C:8]([C:6]1[NH:5][C:4]([C:11]([O:13][CH3:14])=[O:12])=[C:3]([Cl:2])[CH:7]=1)=[O:9]

Komponenten

4

Edukt 2

HCID 222AmmoniaHCID 86644903Methyl 3-chloro-5-(chlorocarbonyl)-1H-pyrrole-2-carboxylate

Produkt 1

HCID 68481017Methyl 5-(aminocarbonyl)-3-chloro-1H-pyrrole-2-carboxylateAusbeute 51,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Ammonia (5.8 mL, 2.9 mmol) was added to a solution of methyl 3-chloro-5-(chlorocarbonyl)-1H-pyrrole-2-carboxylate (0.15 g, 0.58 mmol) in THF and the resulting solution stirred until no starting material was evident by TLC. The solvent was evaporated and purification was accomplished by silica gel column chromatography (30 to 100% EtOAc/hexanes) to afford the title compound (0.060 g, 51%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.29 (br. s., 1H), 7.82 (br. s., 1H), 7.47 (br. s., 1H), 6.80 (s, 1H), 3.77 (s, 3H). LCMS: m/z 201.4 (M−1).

Aufarbeitung

  1. customThe solvent was evaporated
  2. custompurification

Quellen und Nachweise

ORD-Eintrag
ord-208b14809594490db9757216793c72ec
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304419B2

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