p-Toluenesulfonic acid → HCID 14685750, compound

HRID 1088803Notes

Reaction equation

HRID 1088803 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)[CH2:13][CH2:14][N:3]1[C:4]=23.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:27]([NH2:30])[CH:28]=[CH2:29]>CO>[O:1]=[C:2]1[O:7][CH2:6][C:5]2[CH:8]=[CH:9][CH:10]=[C:11]3[CH:12]([NH:30][CH2:27][CH:28]=[CH2:29])[CH2:13][CH2:14][N:3]1[C:4]=23

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7853AllylamineHCID 146857275,6-Dihydro-1H,3H,7H-[1,3]oxazino[5,4,3-ij]quinoline-3,7-dione

Product 1

HCID 14685750HCID 14685750, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6,7-dihydro-3,7-dioxo-1H,3H,5H-pyrido[3,2,1-ij][3,1]benzoxazine (6.10 g) in methanol (100 ml) were added molecular sieve 3A (12 g), p-toluenesulfonic acid (catalytic amount) and allylamine (50 ml), and the mixture was refluxed overnight. After cooling the reaction mixture, molecular sieve 3A was filtered off and sodium borohydride (1.70 g) was added to the filtrate under ice-cooling, then the mixture was stirred for 1 hour at room temperature. To the reaction mixture was added a small amount of water, and methanol was distilled off. The residue was extracted with dichloromethane and dried over anhydrous magnesium sulfate. After distilling off the solvent, the resulting residue was purified by silica gel column chromatography [eluent: n-hexane-ethyl acetate (3:1)]to give 6,7-dihydro-3-oxo-7-allylamino-1H,3H,5H-pyrido[3,2,1-ij][3,1]benzoxazine (5.89 g).

Workup

  1. temperaturethe mixture was refluxed overnight
  2. filtrationwas filtered off
  3. additionsodium borohydride (1.70 g) was added to the filtrate under ice-
  4. temperaturecooling
  5. additionTo the reaction mixture was added a small amount of water, and methanol
  6. distillationwas distilled off
  7. extractionThe residue was extracted with dichloromethane
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationAfter distilling off the solvent
  10. customthe resulting residue was purified by silica gel column chromatography [eluent

Sources & evidence

ORD record
ord-44385a28c5034b43be4d61f975dbab1e
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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