1,3,3-Trimethyl-2-methyleneindoline → HCID 19360917, Verbindung

HRID 374100

Reaktionsgleichung

Reaktionsgleichung von HRID 374100
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH3:12])([CH3:11])[C:3]1=[CH2:13].[OH:14][CH2:15][C:16]1[C:17]([OH:28])=[C:18]([N:26]=O)[C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[CH:21][CH:20]=2>C(O)C>[CH3:1][N:2]1[C:3]2([O:28][C:17]3[C:16]([CH2:15][OH:14])=[CH:25][C:24]4[C:19]([C:18]=3[N:26]=[CH:13]2)=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:4]([CH3:11])([CH3:12])[C:5]2[C:10]1=[CH:9][CH:8]=[CH:7][CH:6]=2

Komponenten

4

Edukt 2

HCID 83511,3,3-Trimethyl-2-methyleneindolineHCID 232862843-Hydroxymethyl-1-nitroso-2-naphthol

Produkt 1

HCID 19360917HCID 19360917, VerbindungAusbeute 20,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

In 100 ml of ethanol, 7.0 g (40 mmol) of 1,3,3-trimethyl-2-methyleneindoline and 8.0 g (40 mmol) of 3-hydroxymethyl-1-nitroso-2-naphthol were dissolved and the solution was heated to reflux for 3 hours. After removal of the solvent, purification was conducted by column chromatography and recrystallization from hexane to obtain 3.0 g of 1,3,3-trimethyl-5'-hydroxymethylspiro [indoline-2,3'-[3H]-naphtho[2,1-b](1,4)oxazine] as a white solid. In 50 ml of methylene dichloride, 1.1 g (3 mmol) of the thus obtained spirooxazine compound was dissolved and 4 ml of triethylamine was added thereto, and then 0.5 g (5 mmol) of methacrylic acid chloride was added dropwise thereto at room temperature and the mixture was allowed to react. After removal of solvent, purification was conducted by column chromatography and recrystallization from hexane to obtain 1.0 g of 1,3,3-trimethyl-5'-methacryloxymethylspiro[indoline-2,3'-[3H]-naphtho[2,1 -b](1,4)oxazine] as a light yellow solid.

Aufarbeitung

  1. temperaturethe solution was heated
  2. temperatureto reflux for 3 hours
  3. customAfter removal of the solvent, purification
  4. customwas conducted by column chromatography and recrystallization from hexane

Quellen und Nachweise

ORD-Eintrag
ord-f8c33322f814485f8f784f215173855e
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05166345

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