Oxalic Acid → HCID 13200217, compound

HRID 1903219Notes

Reaction equation

HRID 1903219 reaction equation
Cl.[CH3:2][N:3]([CH3:7])[CH2:4][CH2:5][SH:6].[H-].[Na+].Cl[C:11]1[C:20]([CH:21]2[CH2:23][CH2:22]2)=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1.[C:24]([OH:29])(=[O:28])[C:25]([OH:27])=[O:26]>CN(C)C=O>[C:24]([OH:29])(=[O:28])[C:25]([OH:27])=[O:26].[CH:21]1([C:20]2[C:11]([S:6][CH2:5][CH2:4][N:3]([CH3:7])[CH3:2])=[N:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 24758Sodium hydrideHCID 25798Captamine HydrochlorideHCID 14001233HCID 14001233, compound

Product 1

HCID 13200217HCID 13200217, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2-dimethylaminoethanethiol hydrochloride (1.7 g.) in dimethylformamide (25 ml.) was added dropwise to a suspension of sodium hydride (0.5 g.) in a solution of 2-chloro-3-cyclopropylquinoline (2.0 g.) in dimethylformamide (25 ml.) at 0°-5°. The mixture was then heated at 80° for 4 hr. and then poured into ice water (200 ml.) and extracted with ethyl acetate (3×100 ml.). The ethyl acetate extract was washed successively with saturated brine (100 ml.) and water (3×100 ml.), dried (Na2SO4), and the solvent evaporated. The residue was chromatographed on silica gel (Merck 9385, 200 g.) using 10% v/v methanol in ethyl acetate as eluant. The appropriate fraction (monitored by thin layer chromatography) was evaporated, dissolved in methanol, and one equivalent of anhydrous oxalic acid was added. The solvent was evaporated and the residue crystallised from methanol/diethyl ether to give 3-cyclopropyl-2-(2-dimethylaminoethylthio)quinoline hydrogen oxalate, m.p. 158°.

Workup

  1. temperatureThe mixture was then heated at 80° for 4 hr
  2. extractionextracted with ethyl acetate (3×100 ml.)
  3. extractionThe ethyl acetate extract
  4. washwas washed successively with saturated brine (100 ml.) and water (3×100 ml.)
  5. dry with materialdried (Na2SO4)
  6. customthe solvent evaporated
  7. customThe residue was chromatographed on silica gel (Merck 9385, 200 g.)
  8. customThe appropriate fraction (monitored by thin layer chromatography) was evaporated
  9. dissolutiondissolved in methanol
  10. customThe solvent was evaporated
  11. customthe residue crystallised from methanol/diethyl ether

Sources & evidence

ORD record
ord-54ec937100624e079da03d78abe5a671
Source dataset
uspto-grants-1984_03
Patent number
US04435405

Reaction notes

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