Formaldehyde → 5-(5-Nitroindol-3-ylmethyl)-2,2-dimethyl-1,3-dioxane4,6-dione

HRID 1769627

Reaktionsgleichung

Reaktionsgleichung von HRID 1769627
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].[CH3:13][C:14]1([CH3:22])[O:21][C:19](=[O:20])[CH2:18][C:16](=[O:17])[O:15]1.[CH2:23]=O>C(#N)C.N1CCC[C@H]1C(O)=O>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:23][CH:18]1[C:19](=[O:20])[O:21][C:14]([CH3:22])([CH3:13])[O:15][C:16]1=[O:17])([O-:3])=[O:2]

Komponenten

6

Edukt 3

HCID 712FormaldehydeHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 225235-Nitroindole

Produkt 1

HCID 152282635-(5-Nitroindol-3-ylmethyl)-2,2-dimethyl-1,3-dioxane4,6-dioneAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 145742L-ProlineKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

An adaption of the procedure of Flaugh1 was used. Thus, a solution of 5-nitroindole (50.0 g, 0.32 mol), Meldrum's acid (46.0 g, 0.32 mol), 37% aqueous formaldehyde (26.0 mL, 0.32 mol) and proline (1.8 g, 0.016 mol) in 200 mL of acetonitrile was stirred at room temperature for 18 h. The resulting thick yellow slurry was filtered and the filtercake was washed with acetonitrile, then acetone and finally with ether. This material was dried in vacuo to give the title compound (80.0 g, 81%) as a bright yellow solid, mp 182° C. (dec). The mother liquor was concentrated and then diluted with H2O, and the resulting solid was collected, washed and dried as before to give a second crop of the product (7.0 g) as a darker yellow solid.

Aufarbeitung

  1. filtrationThe resulting thick yellow slurry was filtered
  2. washthe filtercake was washed with acetonitrile
  3. customThis material was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-14a730b996074dd99abbda8e522881cd
Quelldatensatz
uspto-grants-1995_01
Patentnummer
US05382592

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