Formaldehyde → 5-(4-Methyl-5-nitroindol-3-ylmethyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 441094Notizen

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Reaktionsgleichung von HRID 441094
[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[CH3:14][C:15]1([CH3:23])[O:22][C:20](=[O:21])[CH2:19][C:17](=[O:18])[O:16]1.[CH2:24]=O>C(#N)C.N1CCCC1C(O)=O>[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:24][CH:19]1[C:20](=[O:21])[O:22][C:15]([CH3:23])([CH3:14])[O:16][C:17]1=[O:18])=[CH:5][NH:6]2

Komponenten

6

Edukt 3

HCID 712FormaldehydeHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 154534624-methyl-5-nitro-1H-indole

Produkt 1

HCID 224057085-(4-Methyl-5-nitroindol-3-ylmethyl)-2,2-dimethyl-1,3-dioxane-4,6-dioneAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 614proline dl-formKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

An adaption of the procedure of Flaugh was used. Thus, a solution of 4-methyl-5-nitroindole (0.880 g, 5.00 mmol), Meldrum's acid (0.864 g, 6.00 mmol), 37% aqueous formaldehyde (0.5 mL, 6.0 mmol) and D,L-proline (0.029 g, 0.25 mmol) in 25 mL of acetonitrile was stirred at room temperature for 72 h. The resulting yellow slurry was stored at -20° C. and then the cold mixture was filtered. The filtercake was washed with cold acetonitrile and ether, and then it was dried in vacuo to give the title compound (1.055 g, 64%) as a canary-yellow solid, mp 196°-198° C. (dec): IR (KBr) 3338, 1782, 1742 cm-1 ; 1H NMR (DMSO-d6, 200 MHz) δ 11.46 (br s, 1H), 7.61 (d, J=8.9 Hz, 1H), 7.32 (d, J=8.9 Hz, 1H), 7.25 (d, J= 2.4 Hz, 1H), 4.74 (t, J=5.0 Hz, 1H), 3.64 (d, J=4.9 Hz, 1H), 2.80 (s, 3H), 1.84 (s, 3H), 1.69 (s, 3H). Anal. Calcd for C16H16N2O6 : C, 57.83; H, 4.85; N, 8.43. Found: C, 57.42; H, 4.68; N, 8.52.

Aufarbeitung

  1. customwas stored at -20° C.
  2. filtrationthe cold mixture was filtered
  3. washThe filtercake was washed with cold acetonitrile and ether
  4. customit was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fb25776e0c2548fc9d8ef5183d061b96
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05521188

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