1,2-Dichloroethane → HCID 14851958, compound

HRID 1032779Notes

Reaction equation

HRID 1032779 reaction equation
[NH:1]1C2[C:5](=[CH:6][CH:7]=[CH:8]C=2)[CH2:4][CH2:3][C:2]1=[O:11].Cl[CH2:13][CH2:14][Cl:15].[Cl:16]Cl.[OH-].[NH4+]>C(O)=O.Cl>[Cl:16][C:7]1[CH:6]=[C:5]2[C:13](=[C:14]([Cl:15])[CH:8]=1)[NH:1][C:2](=[O:11])[CH2:3][CH2:4]2

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 14923Ammonium HydroxideHCID 24526Chlorine2×HCID 64796Hydrocarbostyril

Product 1

HCID 14851958HCID 14851958, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A solution of 6 g of 3,4-dihydro-2(1H)-quinolinone in 50 ml of formic acid and 50 ml of conc. hydrochloric acid was added to 75 ml of 1,2-dichloroethane which had been saturated with chlorine. The mixture was stirred over ice for 30 minutes. Chlorine was introduced for 5 minutes and stirring in the cold was continued for 2 hours. It was then poured onto ice, was made basic with ammonium hydroxide and was extracted with methylene chloride. The extracts were dried and evaporated and the residue was chromatographed over 300 g of silica gel using 8% (v/v) of ethyl acetate in methylene chloride. Crystallization of the combined clean fractions from ether gave colorless crystals of 6,8-dichloro-3,4-dihydro-2(1H) quinolinone with m.p. 145°-146°.

Workup

  1. stirringstirring in the cold
  2. waitwas continued for 2 hours
  3. additionIt was then poured onto ice
  4. extractionwas extracted with methylene chloride
  5. customThe extracts were dried
  6. customevaporated
  7. customthe residue was chromatographed over 300 g of silica gel using 8% (v/v) of ethyl acetate in methylene chloride
  8. customCrystallization of the combined clean fractions from ether

Sources & evidence

ORD record
ord-e97f534770194c8d9d7d0c80d206d342
Source dataset
uspto-grants-1990_09
Patent number
US04959361

Reaction notes

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