ethyl 5-carbamoyl-4-(3-fluoro-4-nitrophenyl)-1H-pyrrole-3-carboxylate → ethyl 5-cyano-4-(3-fluoro-4-nitrophenyl)-1H-pyrrole-3-carboxylate

HRID 1094846Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1094846
[NH2:1][C:2]([C:4]1[NH:8][CH:7]=[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:5]=1[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[C:16]([F:23])[CH:15]=1)=O>O=P(Cl)(Cl)Cl>[C:2]([C:4]1[NH:8][CH:7]=[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:5]=1[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[C:16]([F:23])[CH:15]=1)#[N:1]

Komponenten

3

Edukt 1

HCID 57955150ethyl 5-carbamoyl-4-(3-fluoro-4-nitrophenyl)-1H-pyrrole-3-carboxylate

Produkt 1

HCID 57758340ethyl 5-cyano-4-(3-fluoro-4-nitrophenyl)-1H-pyrrole-3-carboxylateAusbeute 97,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24813Phosphorus oxychlorideLösungsmittel

Versuchsvorschrift

A solution of intermediate ethyl 5-(aminocarbonyl)-4-(3-fluoro-4-nitrophenyl)-1H-pyrrole-3-carboxylate (36.8 mg, 114.5 mmol) in POCl3 (500 mL) was heated to 70° C. for 2 h. TLC analysis indicated that there was complete conversion of starting material. Excess POCl3 was removed under reduced pressure and the remaining solids were poured over ice. The pH was adjusted to 8 using 5 N NaOH and the solution was filtered. The product was dried over night under reduced pressure to afford a light brown solid (33.85 g, 111.6 mmol) in 97% yield. 1H-NMR (DMSO-d6) δ 13.32 (br s, 1H), 8.21 (app t, J=8.4 Hz, 1H), 7.90 (s, 1H), 7.73 (dd, J=12.4, 2.0 Hz, 1H), 7.51 (m, 1H), 4.13 (q, J=7.2 Hz, 2H), 1.15 (t, J=7.2 Hz, 3H); HPLC RT=3.16 min.

Aufarbeitung

  1. customExcess POCl3 was removed under reduced pressure
  2. additionthe remaining solids were poured over ice
  3. filtrationthe solution was filtered
  4. customThe product was dried over night under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ea7e74f7d2b743beaa5bb143bccbadb3
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08133995B2

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