Potassium Carbonate → HCID 53933818, compound

HRID 613573Notes

Reaction equation

HRID 613573 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[NH:15][CH:14]=[C:13]([CH3:17])[C:12]2=[O:18])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:30](Br)[CH:31]=[CH:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CN1CCCC1=O>[CH2:30]([O:18][C:12]1[C:11]2[C:16](=[C:7]([NH:6][C:4](=[O:5])[C:3]3[C:19]([Cl:23])=[CH:20][CH:21]=[CH:22][C:2]=3[Cl:1])[CH:8]=[CH:9][CH:10]=2)[N:15]=[CH:14][C:13]=1[CH3:17])[CH:31]=[CH:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 98116BromomethylstyreneHCID 19592684HCID 19592684, compound

Product 1

HCID 53933818HCID 53933818, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a suspension of 8-(2,6-dichlorobenzoylamino)-1,4-dihydro-3-methyl-4-oxoquinoline (130 mg), potassium carbonate (155 mg) and N-methylpyrrolidone (3 ml) was added cinnamyl bromide (81.2 mg), and the mixture was stirred for 2.5 hours at ambient temperature. The mixture was extracted with ethyl acetate, and the extract was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was crystallized from ethanol to give 4-cinnamyloxy-8-(2,6-dichlorobenzoylamino)-3-methylquinoline (125 mg) as white crystal.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe extract was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-3628a598341c499c80edad4474090a20
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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