Water → HCID 10601564, compound

HRID 1699205Notes

Reaction equation

HRID 1699205 reaction equation
[H-].[Na+].[Br-].[C:4]1(=[O:35])[N:8]([CH2:9][CH2:10][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:7](=[O:30])[C:6]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:5]12.[Cl:36][C:37]1[C:55]([CH:56]=O)=[CH:54][CH:53]=[C:52]([Cl:58])[C:38]=1[CH2:39][O:40][C:41]1[CH:42]=[CH:43][CH:44]=[C:45]2[C:50]=1[N:49]=[C:48]([CH3:51])[CH:47]=[CH:46]2.O>CS(C)=O>[Cl:36][C:37]1[C:55](/[CH:56]=[CH:10]\[CH2:9][N:8]2[C:4](=[O:35])[C:5]3=[CH:34][CH:33]=[CH:32][CH:31]=[C:6]3[C:7]2=[O:30])=[CH:54][CH:53]=[C:52]([Cl:58])[C:38]=1[CH2:39][O:40][C:41]1[CH:42]=[CH:43][CH:44]=[C:45]2[C:50]=1[N:49]=[C:48]([CH3:51])[CH:47]=[CH:46]2.[Cl:36][C:37]1[C:55](/[CH:56]=[CH:10]/[CH2:9][N:8]2[C:4](=[O:35])[C:5]3=[CH:34][CH:33]=[CH:32][CH:31]=[C:6]3[C:7]2=[O:30])=[CH:54][CH:53]=[C:52]([Cl:58])[C:38]=1[CH2:39][O:40][C:41]1[CH:42]=[CH:43][CH:44]=[C:45]2[C:50]=1[N:49]=[C:48]([CH3:51])[CH:47]=[CH:46]2

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 10831411HCID 10831411, compoundHCID 18321849(2-Phthalimidoethyl)triphenylphosphonium bromide

Product 2

HCID 10601564HCID 10601564, compoundHCID 10625295HCID 10625295, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

The mixture of 60% sodium hydride in oil (56 mg) and dimethyl sulfoxide (6 ml) was stirred at 60° C. under nitrogen atmosphere for 1 hour. To the mixture was added (2-phthalimidoethyl)triphenylphosphonium bromide (1.19 g) at ambient temperature, and the mixture was stirred for 30 minutes. To the mixture was added 8-(2,6-dichloro-3-formylbenzyloxy)-2-methylquinoline (400 mg) under water bath cooling, and the mixture was stirred overnight. To the reaction mixture was added water and extracted with chloroform. The organic layer was washed with water three times and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash silica gel chromatography eluted with n-hexane-ethyl acetate to give 8-[2,6-dichloro-3-((Z)-3-phthalimido-1-propenyl)benzyloxy]-2-methylquinoline as amorphous first and 8-[2,6-dichloro-3-((E)-3-phthalimido-1-propenyl)benzyloxy]-2-methylquinoline as amorphous second. The former was crystallized from diisopropyl ether to afford pale yellow crystals (138 mg). The latter was crystallized from diisopropyl ether to afford pale yellow crystals (192 mg).

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. temperaturecooling
  3. stirringthe mixture was stirred overnight
  4. extractionextracted with chloroform
  5. washThe organic layer was washed with water three times and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by flash silica gel chromatography
  9. washeluted with n-hexane-ethyl acetate

Sources & evidence

ORD record
ord-50408b04f18a46d18701464bdd61182c
Source dataset
uspto-grants-2002_02
Patent number
US06344462B1

Reaction notes

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