Phosgene → HCID 20477505, compound

HRID 905107Notes

Reaction equation

HRID 905107 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH2:6][C:5]2=[O:12].[C:13](Cl)([Cl:15])=[O:14]>O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:13]([Cl:15])=[O:14])[CH2:7][CH2:6][C:5]2=[O:12]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 11423781HCID 11423781, compound

Product 1

HCID 20477505HCID 20477505, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

33.0 parts of 6-fluoro-4-oxo-1,2,3,4-tetrahydroquinoline and 200 parts of dioxane were mixed, and 39.6 parts of phosgene were introduced to the stirred mixture over about 30 minutes while the temperature was maintained at 20°-25° C. After the introduction, the temperature was raised gradually, and the reaction was effected at 40°-45° C. for 2.5 hours, after which the temperature was further raised to 70° C., nitrogen gas was passed through the mixture, and the solvent (dioxane) was distilled off under reduced pressure. Petroleum ether was added to the residue followed by filtration, washing and drying, and there was obtained 43.7 parts of 6-fluoro-4-oxo-1-chloroformyl-1,2,3,4-tetrahydroquinoline.

Workup

  1. temperaturewas maintained at 20°-25° C
  2. temperatureAfter the introduction, the temperature was raised gradually
  3. distillationthe solvent (dioxane) was distilled off under reduced pressure
  4. additionPetroleum ether was added to the residue
  5. filtrationfollowed by filtration
  6. washwashing
  7. customdrying

Sources & evidence

ORD record
ord-3fa4c40de51f4659b924a845b3d8b5b8
Source dataset
uspto-grants-1983_12
Patent number
US04421919

Reaction notes

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