1,3,3-Trimethyl-2-methyleneindoline → HCID 19360917、化合物

HRID 374100

反応式

HRID 374100 の反応式
[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

参加物

4

反応物 2

HCID 83511,3,3-Trimethyl-2-methyleneindolineHCID 23286284HCID 23286284、化合物

生成物 1

HCID 19360917HCID 19360917、化合物収率 20.9%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f8c33322f814485f8f784f215173855e
出典データセット
uspto-grants-1992_11
特許番号
US05166345

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