Sulfuric Acid → HCID 54022020, compound

HRID 1075187Notes

Reaction equation

HRID 1075187 reaction equation
[O:1]=[C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[CH2:18]([O:20][C:21](=[O:24])[CH2:22]Br)[CH3:19].[OH-].[K+].S(=O)(=O)(O)O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[CH2:18]([O:20][C:21](=[O:24])[CH2:22][N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:2]1=[O:1])[CH3:19]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 7748Ethyl bromoacetateHCID 14797Potassium HydroxideHCID 2828372(1H)-QUINOLINONE, 3-PHENYL-

Product 1

HCID 54022020HCID 54022020, compoundYield 72.6%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

17 g of 1,2-dihydro-2-oxo-3-phenylquinoline, 12.8 g of bromoacetic acid ethyl ester, 2.5 g of tetrabutylammonium bromide and 6.2 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 diethyl ether and the organic phase is dried over sodium sulphate, treated with active charcoal and concentrated. 17.1 g of the title compound are obtained as a viscous, yellow oil.

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialthe organic phase is dried over sodium sulphate
  3. additiontreated with active charcoal
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3fc98738aeca4c1d8aba1c815a1efcba
Source dataset
uspto-grants-1983_07
Patent number
US04395414

Reaction notes

Loading…