Dimethylformamide → HCID 58966768, Verbindung

HRID 2235168

Reaktionsgleichung

Reaktionsgleichung von HRID 2235168
[CH3:1][C:2]1[C:10]([CH3:11])=[CH:9][C:5](C(O)=O)=[CH:4][C:3]=1[N+:12]([O-])=O.C[O:16][CH:17]([O:21][CH3:22])N(C)C.O.NN.[CH3:26]N(C)C=O>CO.[Ni]>[CH3:22][O:21][C:17]([C:5]1[CH:4]=[C:3]2[C:2]([CH:1]=[CH:26][NH:12]2)=[C:10]([CH3:11])[CH:9]=1)=[O:16]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 24654Hydrazine hydrate (1:1)HCID 78373Dimethylformamide dimethyl acetalHCID 113675723,4-Dimethyl-5-nitrobenzoic acid

Produkt 1

HCID 58966768HCID 58966768, VerbindungAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 4,5-dimethyl-3-nitrobenzoic acid (Helv. Chim. Acta 1980, 37, 385; 2.50 g, 12.8 mmol) and N,N-dimethylformamide dimethyl acetal (3.66 g, 30.7 mmol) in N,N-dimethylformamide (25 mL) was heated at 140° C. for 4 h, then volatile material was removed by distillation. The residue was taken up in tetrahydrofuran (10 mL) and methanol (10 mL), then Raney nickel (aqueous suspension, 1 mL) and hydrazine hydrate (1.85 g, 57.6 mmol) were added over 30 min in three portions at 50° C., and the reaction was kept at 50° C. for another 90 min. The reaction mixture was filtered through diatomaceous earth, the filtrate was dried (MgSO4), and evaporated. Chromatography (SiO2, heptane-ethyl acetate 2:1) produced 4-methyl-1H-indole-6-carboxylic acid methyl ester (1.68 g, 69%). White solid, MS (ISP): m/e 190.3 (M+H).

Aufarbeitung

  1. customvolatile material was removed by distillation
  2. filtrationThe reaction mixture was filtered through diatomaceous earth
  3. dry with materialthe filtrate was dried (MgSO4)
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c444d1b4de2c45af81f40bc4ca9dd41e
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07713996B2

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