Ammonium Acetate → 2-(Aminomethylidene)-2,3-dihydro-1h-inden-1-one

HRID 461880

Reaktionsgleichung

Reaktionsgleichung von HRID 461880
O[CH:2]1C(=C)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=O.[C:13]([O-:16])(=O)[CH3:14].[NH4+:17]>C(O)C>[NH2:17][CH:2]=[C:3]1[CH2:4][C:5]2[C:14](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:13]1=[O:16]

Komponenten

4

Edukt 2

HCID 517165Ammonium AcetateHCID 706012212-Hydroxy-methylene-1-indanone

Produkt 1

HCID 1703122-(Aminomethylidene)-2,3-dihydro-1h-inden-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-hydroxy-methylene-1-indanone (1.6 kg. as a 3.7 kg. wet cake) dissolved in ethanol (30 liters), and under a nitrogen atmosphere was added ammonium acetate (1.92 kg. 24.8 mole). After eight hours the reaction was complete and the ethanol was removed by vacuum distillation. The reaction mixture was cooled to room temperature and after filtration and air drying (1 hr.) yielded crude 2-aminomethylene-1-indanone (I) as orange crystals. The crystals were then dissolved in a minimum amount of hot ethanol and the solution was decolorized with activated charcoal. Crystals appeared in the filtrate and after cooling overnight at 5° C, the reaction mixture was filtered yielding 960 gm. of compound (I) as light orange crystals. The filtrate was again treated with activated charcoal and recrystallized providing an additional 200 gm. of compound (I). The combined sample (1160 gm.) was milled giving a fine yellowish powder which was dried at 50° C/25 mm/Hg for 48 hours. A sample (50 gm.) of this material was recrystallized three times from ethanol to give 2-aminomethylene-1-indanone (15 gm.), m.p. 166°-168° C.

Aufarbeitung

  1. customthe ethanol was removed by vacuum distillation
  2. filtrationafter filtration and air
  3. customdrying (1 hr.)

Quellen und Nachweise

ORD-Eintrag
ord-c0e3065d575b45bd855dd63e2ea02164
Quelldatensatz
uspto-grants-1977_12
Patentnummer
US04064272

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