Hydrochloric Acid → alpha-Amino-7-ethyl-1H-indole-3-acetic Acid Ethyl Ester

HRID 1788890Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1788890
[CH2:1]([O:3][C:4](=[O:19])[C:5](=[N:17]O)[C:6]1[C:14]2[C:9](=[C:10]([CH2:15][CH3:16])[CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)[CH3:2].Cl>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:19])[CH:5]([NH2:17])[C:6]1[C:14]2[C:9](=[C:10]([CH2:15][CH3:16])[CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)[CH3:2]

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 136393701HCID 136393701, Verbindung

Produkt 1

HCID 14010221alpha-Amino-7-ethyl-1H-indole-3-acetic Acid Ethyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To 7-ethyl-α-(hydroxyimino)-1H-indole-3-acetic acid ethyl ester 5 (7.3 g, 0.028 mol) in ethanol (200 mL) was added concentrated HCl (3 mL) a nd 10% Pd/C (1.0 g). The mixture was hydrogenated at 40 p.s.i. for 4 hours at 22° C. The catalyst and the solvent were removed and the residue was dissolved in water. After washing with methylene chloride, the aqueous phase was basified with 20% sodium hydroxide. The precipitated product, α-amino-7-ethyl-1H-indole-3-acetic acid ethyl ester 6 (6.0 g, 87%), was filtered, washed with water and dried. A sample recrystallized from hot ethanol had m.p. 120°-122° C.

Aufarbeitung

  1. customThe catalyst and the solvent were removed
  2. dissolutionthe residue was dissolved in water
  3. washAfter washing with methylene chloride
  4. filtrationThe precipitated product, α-amino-7-ethyl-1H-indole-3-acetic acid ethyl ester 6 (6.0 g, 87%), was filtered
  5. washwashed with water
  6. customdried
  7. customA sample recrystallized from hot ethanol

Quellen und Nachweise

ORD-Eintrag
ord-bdf81a0e5dcd428ba7545489b8cf51ff
Quelldatensatz
uspto-grants-1987_08
Patentnummer
US04686213

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