1,3,3-Trimethyl-2-methyleneindoline → 1,3-Dihydro-1,3,3-trimethylspiro[2H-indole-2,3'-[3H]naphth[2,1-b][1,4]oxazine]

HRID 1757517Notes

Reaction equation

HRID 1757517 reaction equation
[CH3:1][C:2]1([CH3:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH3:12])[C:3]1=[CH2:4].[N:14]([C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]=1[OH:26])=O>C(O)C>[CH3:12][N:5]1[C:3]2([O:26][C:17]3[CH:18]=[CH:19][C:20]4[C:25]([C:16]=3[N:14]=[CH:4]2)=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:2]([CH3:13])([CH3:1])[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2

Participants

4

Reactant 2

HCID 83511,3,3-Trimethyl-2-methyleneindolineHCID 85801-Nitroso-2-naphthol

Product 1

HCID 5946621,3-Dihydro-1,3,3-trimethylspiro[2H-indole-2,3'-[3H]naphth[2,1-b][1,4]oxazine]

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture 1,3-dihydro-1,3,3-trimethyl-2-methyleneindoline (3.62 g; 0.021 mol) and 1-nitroso-2-naphthol (3.46 g; 0.02 mol) in ethanol (80.0 ml) was heated under reflux for 2 h. The solution was evaporated and the residue flash-chromatographed over silica (dichloromethane) to give 1,3-Dihydro-1,3,3-trimethylspiro[2H-indole-2,3'-3H-naphtho[2,1-b][1,4]oxazine] as a pale yellow solid (3-96 g; 60%).

Workup

  1. temperatureunder reflux for 2 h
  2. customThe solution was evaporated
  3. customthe residue flash-chromatographed over silica (dichloromethane)

Sources & evidence

ORD record
ord-8d511ff5bc2c447fbd50d89bcf30c3fa
Source dataset
uspto-grants-1995_08
Patent number
US05446151

Reaction notes

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