Hydrochloric Acid → HCID 20348480, compound

HRID 442149Notes

Reaction equation

HRID 442149 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([C:12]#N)[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.[C:14]([NH2:17])(=[S:16])C.Cl>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([CH2:12][C:14](=[S:16])[NH2:17])[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 20348480HCID 20348480, compoundYield 63%

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.), and 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 × 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 i vacuo and the residual oil triturated with isopropanol and filtered. Recrystallization 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 × ml)
  4. extractionextracted into methylene chloride (2 × 200 ml.)
  5. dry with materialThe combined extracts were dried (sodium sulphate)
  6. customevaporated i vacuo
  7. customthe residual oil triturated with isopropanol
  8. filtrationfiltered
  9. customRecrystallization from benzene

Sources & evidence

ORD record
ord-0ad4025260484bddb86f5885622f8102
Source dataset
uspto-grants-1977_08
Patent number
US04044138

Reaction notes

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