Ethanol → HCID 67716118, compound

HRID 477706Notes

Reaction equation

HRID 477706 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH2:11][C@@H:12]([C:14]([OH:16])=[O:15])[NH2:13])[CH:2]=1.S(Cl)([Cl:19])=O.[CH2:21](O)[CH3:22]>>[ClH:19].[ClH:19].[CH2:21]([O:15][C:14](=[O:16])[C@H:12]([CH2:11][C:3]1[CH:2]=[N:1][C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH2:13])[CH3:22]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 14840632HCID 14840632, compound

Product 1

HCID 67716118HCID 67716118, compoundYield 90.6%

Procedure

A mixture of 0.45 g (2.08 mmol) of 3-(3-quinolyl)-alanine, 1 mL of thionyl chloride and 20 mL of ethanol was gently refluxed overnight. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in water and treated with active charcoal. Removal of the active charcoal by filtration afforded a filtrate which was evaporated to give a white solid. Crystallization from a mixture of ethanol and ethyl ether gave 0.598 g (90.6%) of the title compound, melting at 204°-205° C. with decomposition. NMR spectrum was consistent with the assigned structure: ##STR90##

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. additiontreated with active charcoal
  4. customRemoval of the active charcoal
  5. filtrationby filtration
  6. customafforded a filtrate which
  7. customwas evaporated
  8. customto give a white solid
  9. customCrystallization
  10. additionfrom a mixture of ethanol and ethyl ether

Sources & evidence

ORD record
ord-311396e73c3942088a1e0908e2724257
Source dataset
uspto-grants-1989_12
Patent number
US04888427

Reaction notes

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