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Sodium hydride → ethyl 1-amino-5-cyano-4-(3-fluoro-4-nitrophenyl)-1H-pyrrole-3-carboxylate

HRID 1094847
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1094847
[C:1]([C:3]1[NH:7][CH:6]=[C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:4]=1[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[C:15]([F:22])[CH:14]=1)#[N:2].[H-].[Na+].[NH2:25]OP(=O)(C1C=CC=CC=1)C1C=CC=CC=1>CN(C=O)C>[NH2:25][N:7]1[C:3]([C:1]#[N:2])=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[C:15]([F:22])[CH:14]=2)[C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 10955453O-(Diphenylphosphinyl)hydroxylamine2×HCID 57758340ethyl 5-cyano-4-(3-fluoro-4-nitrophenyl)-1H-pyrrole-3-carboxylate

Produkt 1

HCID 57757940ethyl 1-amino-5-cyano-4-(3-fluoro-4-nitrophenyl)-1H-pyrrole-3-carboxylateAusbeute 71,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of ethyl 5-cyano-4-(3-fluoro-4-nitrophenyl)-1H pyrrole-3-carboxylate (31.9 g, 105.2 mmol) in DMF (1.5 L) was slowly added NaH (34.54 g, 136.7 mmol). After the evolution of gas had ceased (aminooxy)(diphenyl)phosphine oxide (34.4 g, 147.3 mmol) was added in one portion. Upon addition of (aminooxy)(diphenyl)phosphine oxide the reaction mixture solidified. The reaction mixture was heated to 80° C. during which time the solids broke up and mixture stirred freely. The reaction was heated for 3 h, then cooled and the DMF was removed under reduced pressure. The remaining slurry was dissolved in EtOAc (500 mL) and filtered to remove a majority of the phosphinic acid. The filter cake was washed with EtOAc and the organics were concentrated in vacuo. The product was purified by crystallization from hot ACN to provide a tan solid (24.0 g, 75.31 mmol) in 71% yield. 1H-NMR (DMSO-d6) δ 8.21 (app t, J=8.4 Hz, 1H), 7.73 (s, 1H), 7.71 (dd, J=12.4, 2.0 Hz, 1H), 7.48 (m, 1H), 6.72 (s, 2H), 4.11 (q, J=7.2 Hz, 2H), 1.14 (t, J=7.2 Hz, 3H).

Aufarbeitung

  1. additionwas added in one portion
  2. temperatureThe reaction was heated for 3 h
  3. temperaturecooled
  4. customthe DMF was removed under reduced pressure
  5. dissolutionThe remaining slurry was dissolved in EtOAc (500 mL)
  6. filtrationfiltered
  7. customto remove a majority of the phosphinic acid
  8. washThe filter cake was washed with EtOAc
  9. concentrationthe organics were concentrated in vacuo
  10. customThe product was purified by crystallization from hot ACN

Quellen und Nachweise

ORD-Eintrag
ord-e6e709e23d044c298b503145239239af
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08133995B2

Notizen zur Reaktion

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