1,3,3-Trimethyl-2-methyleneindoline → HCID 10066096, compound

HRID 1651741Notes

Reaction equation

HRID 1651741 reaction equation
[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].[N:14]([C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([OH:26])[CH:24]=2)[CH:19]=[CH:18][C:17]=1[OH:27])=O>C(O)C>[CH3:1][N:2]1[C:3]2([O:27][C:17]3[CH:18]=[CH:19][C:20]4[C:25]([C:16]=3[N:14]=[CH:13]2)=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=4)[C:4]([CH3:11])([CH3:12])[C:5]2[C:10]1=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 83511,3,3-Trimethyl-2-methyleneindolineHCID 13750455HCID 13750455, compound

Product 1

HCID 10066096HCID 10066096, compoundYield 24.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 100 ml of ethanol, 9.2 g (53 mmol) of 1,3,3-trimethyl-2-methyleneindoline and 10 g (53 mmol) of 1-nitroso-2,7-dihydroxynaphthalene were dissolved and the solution was heated to reflux for 3 hours. After removing the solvent, recrystallization was conducted using benzene to obtain 4.5 g of 1,3,3-trimethyl-9'-hydroxyspiro[indoline-2,3'-[3H]-naphtho[2,1-b] (1,4)oxazine] in the form of green-white solid. In 50 ml of methylene dichloride, 1.5 g (4.4 mmol) of the thus obtained spirooxazine compound was dissolved and 0.6 g (6 mmol) of the methacrylic acid chloride was added dropwise at room temperature and the mixture was allowed to react. After removal of the solvent, purification by column chromatography and recrystallization from methanol was conducted to obtain 1.2 g of 1,3,3-trimethyl-9'-methacryloxyspiro[indoline-2,3'-[3H]-naphtho-[2,1-b] (1,4)oxazine] as white solid.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 3 hours
  3. customAfter removing
  4. customthe solvent, recrystallization

Sources & evidence

ORD record
ord-c882fb0a68534a36bbcdef561bc2f9a6
Source dataset
uspto-grants-1990_05
Patent number
US04929693

Reaction notes

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