Dichloromethane → HCID 21846056, compound

HRID 619120Notes

Reaction equation

HRID 619120 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:13])[C:8](=[O:14])[CH:7]=[C:6]2[CH2:15][CH2:16]O)#[N:2].[Br:18]P(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.ClCCl>C(OCC)C>[Br:18][CH2:16][CH2:15][C:6]1[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([C:1]#[N:2])[CH:4]=2)[N:9]([CH3:13])[C:8](=[O:14])[CH:7]=1

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 70579Triphenylphosphine dibromideHCID 21846057HCID 21846057, compound

Product 1

HCID 21846056HCID 21846056, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

0.24 g (1.05 mmol) of 6- cyano-4-(2-hydroxyethyl)-1-methyl-2(1H)-quinolone is added in small amounts to 0.48 g (1.14 mmol) of dibromotriphenylphosphorane in 14 ml of dichdoromethane at room temperature. After 75 minutes of stirring at room temperature, the reaction medium is poured into 200 ml of dichloromethane and the mixture is washed with water. The organic phase is dried over sodium sulphate, filtered and condensed under vacuum. The white residue is ground in diethylether. The solid obtained is taken up in a minimum of dichloromethane, the mixture is filtered rapidly through a layer of silica, eluting with ether, and the filtrate is evaporated.

Workup

  1. washthe mixture is washed with water
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. filtrationfiltered
  4. customcondensed under vacuum
  5. customThe solid obtained
  6. filtrationthe mixture is filtered rapidly through a layer of silica
  7. washeluting with ether
  8. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-676df577da584d96b58a1146095ef8b2
Source dataset
uspto-grants-1999_09
Patent number
US05958924

Reaction notes

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