Hydrochloric Acid → 5,6,7,8-Tetrahydro-3-methyl-8-quinolinecarbothioamide

HRID 596484Notes

Reaction equation

HRID 596484 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([C:12]#[N:13])[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.C(N)(=[S:16])C.Cl>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([C:12](=[S:16])[NH2:13])[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723949ThioacetamideHCID 122782108-Cyano-3-methyl-5,6,7,8-tetrahydroquinoline

Product 1

HCID 30039215,6,7,8-Tetrahydro-3-methyl-8-quinolinecarbothioamideYield 63.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Methyl-8-cyano-5,6,7,8-tetrahydroquinoline (1.7 g., 0.01 m.) and thioacetamide (1.5 g., 0.02 m.) were dissolved in dimethylformamide (50 ml.), the solution saturated with dry hydrogen chloride gas and then heated on a steam bath for 4 hours. The cooled reaction mixture was poured onto water (200 ml.), washed with ethyl acetate (2 × 200 ml.) and the extracts discarded. The aqueous solution was adjusted to pH 10.0 with 46% sodium hydroxide and extracted into methylene chloride (2 × 200 ml.). The combined extracts were dried (sodium sulphate), evaporated in vacuo and the residual oil triturated with isopropanol and filtered. Recrystallisation from benzene gave the title compound as pale yellow needles (1.3 g., 63%) m.p. 149°.

Workup

  1. customThe cooled reaction mixture
  2. additionwas poured onto water (200 ml.)
  3. washwashed with ethyl acetate (2 × 200 ml.)
  4. extractionextracted into methylene chloride (2 × 200 ml.)
  5. dry with materialThe combined extracts were dried (sodium sulphate)
  6. customevaporated in vacuo
  7. customthe residual oil triturated with isopropanol
  8. filtrationfiltered
  9. customRecrystallisation from benzene

Sources & evidence

ORD record
ord-b7ffdde5d34348659170e68c22d0398a
Source dataset
uspto-grants-1977_03
Patent number
US04011225

Reaction notes

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