Sodium Hydroxide → HCID 14848353, compound

HRID 2106629

Reaction equation

HRID 2106629 reaction equation
[I-].[CH3:2][N+:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]3=2)[C:5]([CH3:17])([CH3:16])[C:4]=1[CH3:18].[OH-].[Na+].[CH3:21][O:22][C:23]1[CH:32]=[C:31]2[C:26]([CH:27]=[CH:28][C:29]([OH:35])=[C:30]2[N:33]=O)=[CH:25][CH:24]=1>CCCCCC>[CH3:21][O:22][C:23]1[CH:32]=[C:31]2[C:26]([CH:27]=[CH:28][C:29]3[O:35][C:4]4([C:5]([CH3:17])([CH3:16])[C:6]5[C:11](=[C:10]6[CH:12]=[CH:13][CH:14]=[CH:15][C:9]6=[CH:8][CH:7]=5)[N:3]4[CH3:2])[CH:18]=[N:33][C:30]=32)=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 28330807-Methoxy-1-nitrosonaphthalen-2-olHCID 13627405HCID 13627405, compound

Product 1

HCID 14848353HCID 14848353, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a solution of 1.05 grams (3.0 mmole) of 1,2,3,3-tetramethyl-3H-benz[g] indolium iodide in 15 milliliters (ml) of hexane at 25° C. was added 10 ml (50 mmole) of 20% sodium hydroxide. The two phase mixture was stirred vigorously under nitrogen for about 30 minutes. The organic layer was separated, transferred to a reaction flask equipped with a reflux condenser and diluted with 15 ml of absolute ethanol. To this solution was added 0.61 grams (3.0 mmole) of 7-methoxy-1-nitroso-2-naphthol and the resulting reaction mixture refluxed under nitrogen for about 6 hours. The reaction mixture was cooled, the volume reduced under vacuum and 0.29 grams (0.71 mmole) of the product, 9'-methoxy-1,3,3-trimethylspiro [benz[g] indoline-2,3'-[3H] naphth [2,1-b][1,4] oxazine] was obtained as yellow-orange crystals. A solution of the crystals dissolved in ethanol or toluene was colorless. The solution turned blue when irradiated with ultraviolet light.

Workup

  1. customThe organic layer was separated
  2. customtransferred to a reaction flask
  3. customequipped with a reflux condenser
  4. additiondiluted with 15 ml of absolute ethanol
  5. customthe resulting reaction mixture
  6. temperaturerefluxed under nitrogen for about 6 hours
  7. temperatureThe reaction mixture was cooled

Sources & evidence

ORD record
ord-e650af34ceed47e782b3d534b444c563
Source dataset
uspto-grants-1990_06
Patent number
US04931219

Linked notes

Loading…