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

HRID 436485Notes

Reaction equation

HRID 436485 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 (1g.) 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-df541f56158b4ff7bcdd0d9b6b817e25
Source dataset
uspto-grants-1977_02
Patent number
US04009169

Reaction notes

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