Benzene → HCID 53890094, compound

HRID 414428Notes

Reaction equation

HRID 414428 reaction equation
[I-].[O:2]([CH2:9][CH:10]1[NH+:14]([CH3:15])[C:13]([CH3:17])([CH3:16])[CH2:12][O:11]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1C=CC=CC=1.C(N(CC)CC)C.[N:31]([C:33]1[C:42]([OH:43])=[CH:41][CH:40]=[C:39]2[C:34]=1[CH:35]=[CH:36][CH:37]=[N:38]2)=O>O>[O:2]([C:9]1[C:10]2([N:14]([CH3:15])[C:13]([CH3:17])([CH3:16])[CH2:12][O:11]2)[O:43][C:42]2[CH:41]=[CH:40][C:39]3[N:38]=[CH:37][CH:36]=[CH:35][C:34]=3[C:33]=2[N:31]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 8471TriethylamineHCID 2795985-nitrosoquinolin-6-olHCID 21280651HCID 21280651, compound

Product 1

HCID 53890094HCID 53890094, compoundYield 2.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a dry 250 ml three-necked flask kept under dry nitrogen and fitted with a distillation column and internal thermometer was added 2-phenoxymethyl-3,4,4-trimethyl-1,3-oxazolidinium iodide (6.00 grams, 18.1 mmole) and 80 ml dry benzene. To the heterogeneous stirred solution was added in one portion triethylamine (3.64 grams, 36 mmole) followed by 5-nitroso-6-quinolinol (2.61 grams, 15 mmole). The solution was heated to reflux and maintained at reflux for 3 hours during which time water that formed during the course of the reaction was azeotropically removed. The solution was cooled with stirring overnight, decanted away from the tarry residue, and concentrated in vacuo. The product was isolated by flash chromatography to yield 0.16 grams of 2'-phenoxy-3,4,4-trimethylspiro[oxazolidine-2,3'-[3H]pyrido[3,2-f] [1,4]benzoxazine], which was characterized by appropriate spectral techniques. A toluene solution of the product changed to red when irradiated with ultraviolet light. The solution returned to its original hue after the UV light was removed.

Workup

  1. customInto a dry 250 ml three-necked flask kept under dry nitrogen
  2. customfitted with a distillation column and internal thermometer
  3. temperatureThe solution was heated
  4. temperatureto reflux
  5. temperaturemaintained
  6. customformed during the course of the reaction
  7. customwas azeotropically removed
  8. temperatureThe solution was cooled
  9. customdecanted away from the tarry residue
  10. concentrationconcentrated in vacuo
  11. customThe product was isolated by flash chromatography

Sources & evidence

ORD record
ord-a0223fa9d4fa415b81c229de18947dc9
Source dataset
uspto-grants-1988_12
Patent number
US04792224

Reaction notes

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