2-Benzofurancarboxylic acid, 5-nitro-, ethyl ester → Ethyl 5-aminobenzofuran-2-carboxylate

HRID 1480534

Reaktionsgleichung

Reaktionsgleichung von HRID 1480534
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][C:8]=2[CH:17]=1)([O-])=O>CCO.C1COCC1.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][C:8]=2[CH:17]=1

Komponenten

5

Edukt 1

HCID 13829542-Benzofurancarboxylic acid, 5-nitro-, ethyl ester

Produkt 1

HCID 9837138Ethyl 5-aminobenzofuran-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Ethyl 5-nitrobenzofuran-2-carboxylate (Aldrich, 8.0 g) was dissolved in a mixture of EtOH and THF, treated with 10% Pd/C (wet, Degussa type E101, Aldrich) and hydrogenated on a Parr apparatus at 35 psi for 4 h. The reaction mixture was filtered over Celite, washed with THF and EtOH and concentrated under vacuum to give crude solid product, 6.3 g which was used without purification. 1H NMR (CDCl3) 7.34-7.37 (m, 2H), 6.87 (d, 1H), 6.81 (dd, 1H), 4.41 (q, 2H, OCH2), 3.60 (broad s, 2H, NH2), 1.40 (t, 3H, OCH2CH3); m/z 206.39 [M+H]+

Aufarbeitung

  1. filtrationThe reaction mixture was filtered over Celite
  2. washwashed with THF and EtOH
  3. concentrationconcentrated under vacuum
  4. customto give crude solid product, 6.3 g which
  5. customwas used without purification

Quellen und Nachweise

ORD-Eintrag
ord-b8502854bb9f4cec8001f92442430486
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09409884B2

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