Phosgene → 5,6-Dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

HRID 1440697Notes

Reaction equation

HRID 1440697 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][CH2:9][CH2:8][CH2:7]2.[C:12](Cl)(Cl)=[O:13]>C(O)(=O)C.ClC1C=CC=CC=1>[NH:1]1[C:2]2=[C:11]3[C:6](=[CH:5][CH:4]=[CH:3]2)[CH2:7][CH2:8][CH2:9][N:10]3[C:12]1=[O:13]

Participants

5

Reactant 2

HCID 6371PhosgeneHCID 1046728-Quinolinamine, 1,2,3,4-tetrahydro-

Product 1

HCID 156467025,6-Dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-oneYield 88%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7964ChlorobenzeneSolvent

Procedure

To a solution of 10.77 g of 8-amino-1,2,3,4-tetrahydroquinoline in glacial acetic acid (30 ml) was added dropwise a 21.75% solution of phosgene in chlorobenzene (30 ml), under nitrogen, with stirring. After the addition was complete, the mixture was heated under reflux, with stirring for one hr and evaporated. The residue was taken up in 10% ammonium hydroxide solution (75 ml) and extracted with dichloromethane. The organic extracts were dried over anhydrous magnesium sulfate, filtered, and the filtrate was evaporated. Ether was added to the residue and the mixture was chilled. The precipitate was collected to give 11.2 g (88%) of product.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was heated
  3. temperatureunder reflux
  4. stirringwith stirring for one hr
  5. customevaporated
  6. extractionextracted with dichloromethane
  7. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe filtrate was evaporated
  10. additionEther was added to the residue
  11. temperaturethe mixture was chilled
  12. customThe precipitate was collected

Sources & evidence

ORD record
ord-52d3dacd75fb4f1fb3f748cb1c57aa68
Source dataset
uspto-grants-1996_03
Patent number
US05500423

Reaction notes

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