Acetone → Spiro[2H-indole-2,3'-[3H]naphth[2,1-b][1,4]oxazine], 6'-(2,3-dihydro-1H-indol-1-yl)-1,3-dihydro-1,3,3-trimethyl-

HRID 1757516

Reaction equation

HRID 1757516 reaction equation
[N:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[OH:13])=O.[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15]1.[CH3:23][C:24]1([CH3:35])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]([CH3:34])[C:25]1=[CH2:26].CC(C)=O>ClC=C(Cl)Cl>[CH3:34][N:27]1[C:25]2([O:13][C:4]3[CH:5]=[C:6]([N:14]4[C:22]5[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=5)[CH2:16][CH2:15]4)[C:7]4[C:12]([C:3]=3[N:1]=[CH:26]2)=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:24]([CH3:35])([CH3:23])[C:33]2[C:28]1=[CH:29][CH:30]=[CH:31][CH:32]=2

Participants

6

Reactant 4

HCID 180AcetoneHCID 83511,3,3-Trimethyl-2-methyleneindolineHCID 85801-Nitroso-2-naphtholHCID 10328Indoline

Product 1

HCID 3104873Spiro[2H-indole-2,3'-[3H]naphth[2,1-b][1,4]oxazine], 6'-(2,3-dihydro-1H-indol-1-yl)-1,3-dihydro-1,3,3-trimethyl-

Reagents, catalysts & solvents 1

HCID 6575TrichloroethyleneSolvent2×

Procedure

A mixture of 1-nitroso-2-naphthol (17.3 g; 0.10 mol) and indoline (23.8 g; 0.20 mol) in trichloroethylene (150 ml) was heated under reflux for 10 min. A solution of 1,3-dihydro-1,3,3-trimethyl-2-methyleneindoline (17.3 g; 0.1 mol) in trichloroethylene (100 ml) was added in one batch and the resulting mixture heated under reflux for 1 h. The solution was evaporatedand the oily residue treated with acetone to yield 1,3-Dihydro-1,3,3-trimethyl-6'-(2,3-dihydroindol-1-yl)spiro [2H-indole-2,3'-3H-naphtho[2,1-b][1,4]oxazine] as a yellow solid (4.44 g; 10%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 10 min
  3. temperaturethe resulting mixture heated
  4. temperatureunder reflux for 1 h

Sources & evidence

ORD record
ord-c42abaf123a04f8b98be6ea8403dee48
Source dataset
uspto-grants-1995_08
Patent number
US05446151

Linked notes

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