Dimethylformamide → 2-chloro-5-(5-methyl-1H-pyrazol-3-yl)-benzoic acid methyl ester

HRID 456873Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 456873
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([C:10](=O)[CH3:11])[CH:7]=[CH:6][C:5]=1[Cl:13].CO[C:17](OC)([N:19](C)C)[CH3:18].C[N:25](C)C=O>CN(C)C(=O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([C:10]2[CH:11]=[C:17]([CH3:18])[NH:19][N:25]=2)[CH:7]=[CH:6][C:5]=1[Cl:13]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 58818179Methyl 5-acetyl-2-chlorobenzoate

Produkt 1

HCID 588181962-chloro-5-(5-methyl-1H-pyrazol-3-yl)-benzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

A solution of 5-acetyl-2-chloro-benzoic acid methyl ester (1.58 g, 7.5 mmol) and N,N-dimethylacetamide dimethylacetal in N,N-dimethylformamide and N,N-dimethylacetamide was stirred at 90° C. for 3 h. The mixture was cooled to room temperature and concentrated in vacuo. The residue was diluted with ethanol (18 mL) and tetrahydrofuran (2 mL). Hydrazine hydrate (0.34 mL) was added and the mixture was stirred at room temperature for 16 h. The mixture was concentrated in vacuo. The residue was purified by flash column chromatography (gradient 0–10% methanol-ethyl acetate) to afford the title compound (1.0 g).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with ethanol (18 mL) and tetrahydrofuran (2 mL)
  3. additionHydrazine hydrate (0.34 mL) was added
  4. concentrationThe mixture was concentrated in vacuo
  5. customThe residue was purified by flash column chromatography (gradient 0–10% methanol-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-f7856af6d0ad42eb82cb6ab1c049073a
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186742B2

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