Chloroform → HCID 14624973, compound

HRID 703446Notes

Reaction equation

HRID 703446 reaction equation
O[CH2:2][CH2:3][CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6](=[O:14])[CH2:5]1.S(Cl)([Cl:17])=O.C(Cl)(Cl)Cl>N1C=CC=CC=1.O>[Cl:17][CH2:2][CH2:3][CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6](=[O:14])[CH2:5]1

Participants

6

Reactant 3

HCID 6212ChloroformHCID 24386Thionyl ChlorideHCID 14624972(+/-)-4-(2-hydroxyethyl)-3,4-dihydro-2(1H)-quinolinone

Product 1

HCID 14624973HCID 14624973, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 962WaterSolvent

Procedure

A mixture of 5.2 g (0.027 mol) of (±)-4-(2-hydroxyethyl)-3,4-dihydro-2(1H)-quinolinone, 15 g (0.126 mol) of thionyl chloride, 200 ml of dry chloroform and 10 drops of pyridine is heated to reflux for 4 h. After the mixture is cooled, 50 ml of water are added dropwise and the mixture is stirred for 30 minutes. The organic phase is separated after settling has taken place, dried over magnesium sulphate and concentrated under vacuum. The residue is chromatographed on a silica column. Elution with a dichloromethane/acetone (90:10) mixture yields an oil which is crystallized in cyclohexane. 5 g (88%) of (±)-4-(2-chloroethyl)-3,4-dihydro-2(1H)-quinolinone, melting point 112°-113° C., are obtained.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 4 h
  3. temperatureAfter the mixture is cooled
  4. customThe organic phase is separated after settling
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under vacuum
  7. customThe residue is chromatographed on a silica column
  8. washElution with a dichloromethane/acetone (90:10) mixture
  9. customyields an oil which
  10. customis crystallized in cyclohexane

Sources & evidence

ORD record
ord-f27660ff1f8e46a79d661309c3e4dcde
Source dataset
uspto-grants-1991_01
Patent number
US04983607

Reaction notes

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