Ethanol → HCID 67716118, compound

HRID 1684409Notes

Reaction equation

HRID 1684409 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: ##STR73##

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-63e54005889b435bb28b644ef7742d0b
Source dataset
uspto-grants-1997_06
Patent number
US05639885

Reaction notes

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