Sulfuric Acid → HCID 13180324, compound

HRID 1075186Notes

Reaction equation

HRID 1075186 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[CH2:19]([O:21][C:22](=[O:25])[CH2:23]Br)[CH3:20].[OH-].[K+].S(=O)(=O)(O)O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[CH2:19]([O:21][C:22](=[O:25])[CH2:23][N:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:11]=2)[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]1=[O:12])[CH3:20]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 7748Ethyl bromoacetateHCID 14797Potassium HydroxideHCID 122780387-chloro-3-phenyl-1H-quinolin-2-one

Product 1

HCID 13180324HCID 13180324, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

18 g of 7-chloro-1,2-dihydro-2-oxo-3-phenylquinoline, 11.7 g of bromoacetic acid ethyl ester, 2.3 g of tetrabutylammonium bromide and 5.6 g of powdered potassium hydroxide are stirred in 250 ml of tetrahydrofuran at room temperature for 16 hours. The mixture is poured into 1 l of ice-water, acidified to pH 3 to 4 with dilute sulphuric acid and extracted with methylene chloride (2×200 ml) and the organic phase is dried over sodium sulphate and concentrated. The solid brown residue is stirred with 100 ml of cyclohexane, filtered off and recrystallised from ethanol. 10.0 g of the title compound of m. 142°-143° C. are obtained.

Workup

  1. extractionextracted with methylene chloride (2×200 ml)
  2. dry with materialthe organic phase is dried over sodium sulphate
  3. concentrationconcentrated
  4. filtrationfiltered off
  5. customrecrystallised from ethanol
  6. custom142°-143° C. are obtained

Sources & evidence

ORD record
ord-ba43af6751a7400f9551f405c9655e84
Source dataset
uspto-grants-1983_07
Patent number
US04395414

Reaction notes

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