Ethylene Glycol → HCID 14685731, compound

HRID 1088792Notes

Reaction equation

HRID 1088792 reaction equation
[O:1]=[C:2]1[O:7][CH2:6][C:5]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:12](=[O:15])[CH2:13][CH2:14][N:3]1[C:4]=23.[CH2:16](O)[CH2:17][OH:18].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:1]=[C:2]1[O:7][CH2:6][C:5]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:12]4([O:18][CH2:17][CH2:16][O:15]4)[CH2:13][CH2:14][N:3]1[C:4]=23

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 146857275,6-Dihydro-1H,3H,7H-[1,3]oxazino[5,4,3-ij]quinoline-3,7-dione

Product 1

HCID 14685731HCID 14685731, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 6,7-dihydro-3,7-dioxo-1H,3H,5H-pyrido [3,2,1-ij][3,1]benzoxazine (2 g), ethylene glycol (2.2 ml) and p-toluenesulfonic acid (catalytic amount) in toluene (60 ml) was refluxed by use of Dean-Stark apparatus for 3 hours. After washing the reaction mixture with a saturated aqueous solution of sodium hydrocarbonate, the mixture was dried over anhydrous magnesium sulfate. The solvent was distilled off to give 6,7-dihydro-3-oxo-7,7-ethylenedioxy-1H,3H,5H-pyrido[3,2,1-ij][3,1]benzoxazine (2.1 g).

Workup

  1. washAfter washing the reaction mixture with a saturated aqueous solution of sodium hydrocarbonate
  2. dry with materialthe mixture was dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-b0484b031c9349518a7fc02cad1a099b
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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