(E)-Methyl 4-(2-(dimethylamino)vinyl)-3-nitrobenzoate → Methyl indole-6-carboxylate

HRID 1198954

Reaktionsgleichung

Reaktionsgleichung von HRID 1198954
CN(C)/[CH:3]=[CH:4]/[C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[N+:15]([O-])=O>O1CCCC1.[Pd]>[NH:15]1[C:6]2[C:5](=[CH:14][CH:13]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[CH:7]=2)[CH:4]=[CH:3]1

Komponenten

4

Edukt 1

HCID 894337(E)-Methyl 4-(2-(dimethylamino)vinyl)-3-nitrobenzoate

Produkt 1

HCID 639844Methyl indole-6-carboxylateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of methyl E-4-(2-dimethylaminovinyl)-3-nitrobenzoate (5.58 g) in tetrahydrofuran (100 ml) was hydrogenated at 3.45 bar in the presence of 10% (w/w) palladium on carbon (1.1 g) for 35 minutes. The catalyst was removed by filtration through diatomaceous earth and the filtrate was evaporated. The residue was dissolved in ethyl acetate and the solution obtained was washed successively with 10% (v/v) hydrochloric acid, water, and brine, then dried (MgSO4) and evaporated to give methyl indole-6-carboxylate (3.32 g, 85%) as a white solid; NMR (80 MHz, CDCl3) 3.92(s, 3H, OCH3), 6.57(m, 1H, H3 -indole), 7.32(t, 1H, H2 -indole), 7.10(d, 1H, H4 -indole), 7.87(dd, 1H, H5 -indole), 8.16(broad s, 1H, H7 -indole).

Aufarbeitung

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. customthe solution obtained
  5. washwas washed successively with 10% (v/v) hydrochloric acid, water, and brine
  6. dry with materialdried (MgSO4)
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-3d146358e1924c63b1ca95084f321921
Quelldatensatz
uspto-grants-1990_02
Patentnummer
US04898863

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