Oxalic acid dihydrate → 3-Methyl-5,6,7,8-tetrahydroquinoline-8-thiocarboxamide oxalate

HRID 437470Notes

Reaction equation

HRID 437470 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.O.O.[C:17]([OH:22])(=[O:21])[C:18]([OH:20])=[O:19]>C(O)C>[C:17]([OH:22])(=[O:21])[C:18]([OH:20])=[O:19].[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 61373Oxalic acid dihydrateHCID 30039215,6,7,8-Tetrahydro-3-methyl-8-quinolinecarbothioamide

Product 1

HCID 203583943-Methyl-5,6,7,8-tetrahydroquinoline-8-thiocarboxamide oxalate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 3-methyl-5,6,7,8-tetrahydroquinoline-8-thiocarboxamide (1 g.) in hot ethanol (10 ml.) was added a solution of oxalic acid dihydrate (650 mg.) in hot ethanol (6.5 ml.). The solution was filtered and allowed to cool when the oxalate crystallised. The oxalate was removed by filtration, washed with ether and dried. Yield 1 g. 186°-8° C. Found: C, 52.71%; H, 5.63%; N, 9.19%. Calc. for C13H16N2O4S : C, 52.70%; H, 5.44%; N, 9.46%.

Workup

  1. filtrationThe solution was filtered
  2. temperatureto cool when the oxalate
  3. customcrystallised
  4. customThe oxalate was removed by filtration
  5. washwashed with ether
  6. customdried
  7. custom186°-8° C

Sources & evidence

ORD record
ord-a7c81952c2f243e0821326c435d06959
Source dataset
uspto-grants-1977_06
Patent number
US04031102

Reaction notes

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