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Water → 2-{2-[3-Methoxy-4-(2-hydroxy-3-methacryloyloxypropyloxy)-phenyl]-ethenyl}-quinoline

HRID 326174
Notes
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Reaction equation

HRID 326174 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)=[CH:4][C:3]=1[O:20][CH3:21].[C:22]([O:27][CH2:28][CH:29]1[O:31][CH2:30]1)(=[O:26])[C:23]([CH3:25])=[CH2:24].O>CN(C)C(=O)C.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:21][O:20][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[CH:6]=[CH:7][C:2]=1[O:1][CH2:30][CH:29]([OH:31])[CH2:28][O:27][C:22](=[O:26])[C:23]([CH3:25])=[CH2:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 7837Glycidyl methacrylateHCID 6239702-[2-(4-Hydroxy-3-methoxyphenyl)-ethenyl]-quinoline

Product 1

HCID 543279402-{2-[3-Methoxy-4-(2-hydroxy-3-methacryloyloxypropyloxy)-phenyl]-ethenyl}-quinolineYield 50%

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium Chloride
Catalyst
HCID 31374DimethylacetamideSolvent

Procedure

In 5 cm3 of N,N-dimethylacetamide, 2.77 g of the produced quinoline derivative was dissolved and 1.42 g of glycidyl methacrylate and 0.10 g of tetrabutylammonium chloride were added thereto. The resultant mixture was reacted by maintaining it at 90° to 100° C. for 5 hours. The reaction product was mixed with water. The oily substance separated consequently was extracted via ethyl acetate, washed thoroughly with water, and dried. The dry product was distilled to expel the solvent and then separated and purified by silica gel chromatography, to afford 2-{2-[3-methoxy-4-(2-hydroxy-3-methacryloyloxypropyloxy)-phenyl]-ethenyl}-quinoline in a yield of 50%. When this product was recrystallized via ethyl acetatehexane, there was obtained a pure product having a melting point of 119° C. It was identified by elementary analysis and infrared absorption spectrometry.

Workup

  1. temperatureby maintaining it at 90° to 100° C. for 5 hours
  2. customThe oily substance separated consequently
  3. extractionwas extracted via ethyl acetate
  4. washwashed thoroughly with water
  5. customdried
  6. distillationThe dry product was distilled
  7. customseparated
  8. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-937b96f9883c4dc3af7a5c24d204bfd7
Source dataset
uspto-grants-1984_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04444868

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes