2,3-Dihydroxybutanedioic Acid → 3-Methyl-5,6,7,8-tetrahydroquinoline-8-thiocarboxamide tartrate

HRID 436486Notes

Reaction equation

HRID 436486 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([C:12](=[S:14])[NH2:13])[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.[C:15]([OH:24])(=[O:23])[CH:16]([CH:18]([C:20]([OH:22])=[O:21])[OH:19])[OH:17]>C(O)(C)C>[C:20]([CH:18]([CH:16]([C:15]([OH:24])=[O:23])[OH:17])[OH:19])([OH:22])=[O:21].[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([C:12](=[S:14])[NH2:13])[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 8752,3-Dihydroxybutanedioic AcidHCID 30039215,6,7,8-Tetrahydro-3-methyl-8-quinolinecarbothioamide

Product 1

HCID 203583983-Methyl-5,6,7,8-tetrahydroquinoline-8-thiocarboxamide tartrate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

To a solution of 3-methyl-5,6,7,8-tetrahydroquinoline-8-thiocarboxamide (13 g.) in hot isopropylalcohol (130 ml.) was added a solution of 9.5 g. tartaric acid in hot isopropylalcohol (65 ml.). The solution was filtered and allowed to cool. The precipitated crystals of the tartrate were removed by filtration, washed with a little cold isopropyl alcohol and dried. Yield 10.2 g, 158°-160° C, Found: C, 50.56% H, 5.67%; N, 7.90%. Calc. for C15H20N2O6S : C, 50.55%; H, 5.65%; N, 7.86%.

Workup

  1. filtrationThe solution was filtered
  2. temperatureto cool
  3. customThe precipitated crystals of the tartrate were removed by filtration
  4. washwashed with a little cold isopropyl alcohol
  5. customdried
  6. customYield 10.2 g, 158°-160° C, Found

Sources & evidence

ORD record
ord-41834096b23748b5942fb4b706306988
Source dataset
uspto-grants-1977_02
Patent number
US04009169

Reaction notes

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