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

HRID 442147Notes

Reaction equation

HRID 442147 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. m.p. 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

Sources & evidence

ORD record
ord-60e519483f104fe9bede626c85ac2e03
Source dataset
uspto-grants-1977_08
Patent number
US04044138

Reaction notes

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