1,3,3-Trimethyl-2-methyleneindoline → HCID 19388550, compound

HRID 1757518Notes

Reaction equation

HRID 1757518 reaction equation
[CH2:1]([N:3]([CH2:23][CH3:24])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([N:20]=O)=[C:12]([OH:22])[CH:11]=2)=[CH:6][CH:5]=1)[CH3:2].[CH3:25][C:26]1([CH3:37])[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]([CH3:36])[C:27]1=[CH2:28]>CO>[CH3:36][N:29]1[C:27]2([O:22][C:12]3[CH:11]=[C:10]([C:7]4[CH:8]=[CH:9][C:4]([N:3]([CH2:23][CH3:24])[CH2:1][CH3:2])=[CH:5][CH:6]=4)[C:19]4[C:14]([C:13]=3[N:20]=[CH:28]2)=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:26]([CH3:25])([CH3:37])[C:35]2[C:30]1=[CH:31][CH:32]=[CH:33][CH:34]=2

Participants

4

Reactant 2

HCID 83511,3,3-Trimethyl-2-methyleneindolineHCID 22486123HCID 22486123, compound

Product 1

HCID 19388550HCID 19388550, compoundYield 36.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-(p-diethylaminophenyl)-1-nitroso-2 -hydroxynaphthalene (0.85 g; 0.0027 mol) and 1,3-dihydro-1,3,3-trimethyl-2-methyleneindoline (0.5 g; 0.0029 mol) in methanol (60 ml) under nitrogen, was heated under reflux for 24 hours. The solution was then evaporated and chromatographed over silica (1 part diethyl ether to 10 parts pet. ether) to afford 1,3-dihydro-1,3,3-trimethyl-6'-(p-diethylaminophenyl)spiro[2H-indole-2,3'-[3H]naphth[2,1-b][1,4]oxazine] (0.47 g; 36%) as a yellow solid.

Workup

  1. temperatureunder reflux for 24 hours
  2. customThe solution was then evaporated
  3. customchromatographed over silica (1 part diethyl ether to 10 parts pet. ether)

Sources & evidence

ORD record
ord-1c034c0247c747388aad838b1bb9101b
Source dataset
uspto-grants-1995_08
Patent number
US05446151

Reaction notes

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