Ethyl 2-methylacetoacetate → 2-(3-Amino-2-cyano-4-nitrophenyl)-2-methyl-3-oxobutyric acid ethyl ester

HRID 1835092Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1835092
[NH2:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6](Cl)[C:3]=1[C:4]#[N:5].[CH3:14][CH:15]([C:21]([CH3:23])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH2:19]([O:18][C:16](=[O:17])[C:15]([C:6]1[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:2]([NH2:1])[C:3]=1[C:4]#[N:5])([CH3:14])[C:21](=[O:22])[CH3:23])[CH3:20]

Komponenten

6

Edukt 3

HCID 701Ethyl 2-methylacetoacetateHCID 11430Potassium CarbonateHCID 112756272-Amino-6-chloro-3-nitro-benzonitrile

Produkt 1

HCID 112667142-(3-Amino-2-cyano-4-nitrophenyl)-2-methyl-3-oxobutyric acid ethyl esterAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-6-chloro-3-nitrobenzonitrile (1.97 g, 10 mmol) and ethyl 2-methylacetoacetate (3.6 g, 25 mmol) in DMF (10 mL) was added finely powdered K2CO3, and the mixture stirred vigorously for 24 h. The deep red mixture was diluted with EtOAc and washed in turn with 2 M HCl, water and brine. The residue after evaporation was purified by flash chromatography in hexane/EtOAc 3:1 to yield 2-(3-amino-2-cyano-4-nitrophenyl)-2-methyl-3-oxobutyric acid ethyl ester as an oil (1.39 g, 46%), MS (NH3 CI) 323 (M+NH4+), 293 (M+NH4−NO+).

Aufarbeitung

  1. washwashed in turn with 2 M HCl, water and brine
  2. customThe residue after evaporation
  3. customwas purified by flash chromatography in hexane/EtOAc 3:1

Quellen und Nachweise

ORD-Eintrag
ord-7c6e14120e10446ab66a4f3de1eb8da1
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06770639B2

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