3-Nitrobenzaldehyde → [5-(1H-indol-2-yl)-2-methoxy-phenyl]-(3-nitro-benzyl)-amine

HRID 25523

Reaktionsgleichung

Reaktionsgleichung von HRID 25523
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[C:13]1[C:21]1[CH:22]=[CH:23][C:24]([O:28][CH3:29])=[C:25]([NH2:27])[CH:26]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(O)(=O)C>[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[C:13]1[C:21]1[CH:22]=[CH:23][C:24]([O:28][CH3:29])=[C:25]([NH:27][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH:26]=1

Komponenten

7

Edukt 4

HCID 74493-NitrobenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 99002045-(1H-indol-2-yl)-2-methoxy-phenylamine

Produkt 1

HCID 9969559[5-(1H-indol-2-yl)-2-methoxy-phenyl]-(3-nitro-benzyl)-amineAusbeute 15,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-Nitrobenzaldehyde (0.302 g, 2.0 mmol) was added to a stirred mixture of 5-(1H-indol-2-yl)-2-methoxy-phenylamine (0.476 g, 2.0 mmol) in methylene chloride (125 mL), followed by acetic acid (0.2 g). The resulting mixture was stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (0.46 g, 2.2 mmol) was added in one portion, and the resulting homogeneous solution was stirred at room temperature for 3 days. Saturated aqueous sodium bicarbonate solution (100 mL) was added and the mixture was stirred for 2 hours. The mixture was shaken, the organic layer was separated and dried over Na2SO4. The solvent was evaporated to give an orange oil. Recrystallization from ethyl acetate/hexane gave the product (115 mg), mp 160-162° C.

Aufarbeitung

  1. stirringthe resulting homogeneous solution was stirred at room temperature for 3 days
  2. stirringthe mixture was stirred for 2 hours
  3. stirringThe mixture was shaken
  4. customthe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. customThe solvent was evaporated
  7. customto give an orange oil
  8. customRecrystallization from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-d18519828ae54bcbb33480eea0e9956c
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858739B2

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