o-Xylyl bromide → HCID 13879082, compound

HRID 2231797Notes

Reaction equation

HRID 2231797 reaction equation
[CH3:1][C:2]1[C:10]([CH3:12])([CH3:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16]Br.[N:22]([C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][C:25]=1[OH:34])=O.N1CCCCC1>C1(C)C=CC=CC=1>[CH3:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][N:3]1[C:2]2([O:34][C:25]3[CH:26]=[CH:27][C:28]4[C:33]([C:24]=3[N:22]=[CH:1]2)=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:10]([CH3:12])([CH3:11])[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

6

Reactant 4

HCID 6992o-Xylyl bromideHCID 8082PiperidineHCID 85801-Nitroso-2-naphtholHCID 154273H-Indole, 2,3,3-trimethyl-

Product 1

HCID 13879082HCID 13879082, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 100 ml of toluene were dissolved 4.8 g of 2,3,3-trimethylindolenine, 5.6 g of 2-methylbenzyl bromide, 4.7 g of α-nitroso-β-naphthol and 5.0 g of piperidine. Nitrogen gas was bubbled into the solution for 10 minutes and then the solution was refluxed in a nitrogen current for 2 hours. After the reaction, the reaction mixture was concentrated and then column chromatography separation was carried out by using silica gel as a supporting carrier and toluene as a developing solvent. The solvent was removed by distillation and the obtained solid was recrystallized from methanol to obtain a white crystal of 1-(2-methylbenzyl)-3,3-dimethylspiro[indoline-2,3'-[3H]-naphtho[2,1-b](1,4)-oxazine].

Workup

  1. customNitrogen gas was bubbled into the solution for 10 minutes
  2. temperaturethe solution was refluxed in a nitrogen current for 2 hours
  3. customAfter the reaction
  4. concentrationthe reaction mixture was concentrated
  5. customcolumn chromatography separation
  6. customThe solvent was removed by distillation
  7. customthe obtained solid was recrystallized from methanol

Sources & evidence

ORD record
ord-78a2494841b7457ea950ef2b7e1e7ed4
Source dataset
uspto-grants-1988_11
Patent number
US04784474

Reaction notes

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