Pyridine → 8-Methoxy-5-(methylsulfanyl)-1,2,3,4-tetrahydronaphthalen-2-amine

HRID 2058952Notes

Reaction equation

HRID 2058952 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:17][CH3:18])=[C:7]2[C:12]=1[CH2:11][CH:10]([NH:13]C(=O)C)[CH2:9][CH2:8]2.N1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:17][CH3:18])=[C:7]2[C:12]=1[CH2:11][CH:10]([NH2:13])[CH2:9][CH2:8]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 12924806HCID 12924806, compound

Product 1

HCID 1288058-Methoxy-5-(methylsulfanyl)-1,2,3,4-tetrahydronaphthalen-2-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1.0 g. (3.8 mmole) of N-[1,2,3,4-tetrahydro-8-methoxy-5-(methylthio)-2-naphthalenyl]acetamide in 100 ml. of toluene containing 0.474 g. (6 mmole) of pyridine was heated to 65°. Phosphorous pentachloride (1.25 g., 6 mmol.) was added and heating continued for two hours. The toluene was removed under reduced pressure, 200 ml. of methanol was added and the solution stirred overnight at room temperature. The methanol was evaporated and 100 ml. of 1:1 tetrahydrofuran-H2O was added. After 30 minutes the tetrahydrofuran was removed and the aqueous layer was washed with ether. It was made alkaline with ammonium hydroxide and extracted with three portions of methylene chloride. The combined extracts were dried and evaporated to yield as an oil the free base, 1,2,3,4-tetrahydro-8-methoxy-5-(methylthio)-2-naphthalenamine. This was dissolved in ether and treated with excess ethereal hydrogen chloride. The resulting precipitate was removed by filtration and recrystallized from methanol-ethyl acetate-ether to give 0.45 g. of 1,2,3,4-tetrahydro-8-methoxy- 5-(methylthio)-2-naphthalenamine hydrochloride as a white solid, m.p. 290° (dec.).

Workup

  1. temperatureheating
  2. customThe toluene was removed under reduced pressure, 200 ml
  3. additionof methanol was added
  4. customThe methanol was evaporated
  5. additionof 1:1 tetrahydrofuran-H2O was added
  6. customAfter 30 minutes the tetrahydrofuran was removed
  7. washthe aqueous layer was washed with ether
  8. extractionextracted with three portions of methylene chloride
  9. customThe combined extracts were dried
  10. customevaporated

Sources & evidence

ORD record
ord-33395b89811e47ddbbe1542472f5b036
Source dataset
uspto-grants-1982_03
Patent number
US04320148

Reaction notes

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