Acetic Anhydride → N-[2-(6-Amino-7-methoxy-2,3-dihydro-1H-inden-1-ylidene)ethyl]acetamide

HRID 340685Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 340685
[NH2:1][CH2:2][CH:3]=[C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH2:15])[C:11]=2[O:13][CH3:14])[CH2:6][CH2:5]1.C(N(CC)CC)C.[C:23](OC(=O)C)(=[O:25])[CH3:24].C(=O)([O-])O.[Na+]>O1CCCC1>[NH2:15][C:10]1[C:11]([O:13][CH3:14])=[C:12]2[C:7]([CH2:6][CH2:5][C:4]2=[CH:3][CH2:2][NH:1][C:23](=[O:25])[CH3:24])=[CH:8][CH:9]=1

Komponenten

6

Edukt 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 673546943-(2-Aminoethylidene)-4-methoxyindan-5-amine

Produkt 1

HCID 67352334N-[2-(6-Amino-7-methoxy-2,3-dihydro-1H-inden-1-ylidene)ethyl]acetamideAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

3-(2-Aminoethylidene)-4-methoxyindan-5-amine (15.3 mg, 0.076 mmol) and triethylamine (21.2 μL, 0.152 mmol) were dissolved in tetrahydrofuran (0.9 mL), a solution of acetic anhydride (7.18 μL, 0.076 mmol) in tetrahydrofuran (0.1 mL) was added under ice-cooling, and the mixture was stirred for 15 min. To the reaction solution was added saturated aqueous sodium hydrogencarbonate solution. The mixture was extracted with ethyl acetate and washed with saturated brine. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→90/10) to give the title compound (16.2 mg, yield 87%).

Aufarbeitung

  1. temperaturecooling
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→90/10)

Quellen und Nachweise

ORD-Eintrag
ord-0bc4e2645d6a479791fe99c15c426069
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895591B2

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