Hydrochloric Acid → HCID 70387565, compound

The crude ethyl 6-(chloromethyl)-1,2,3,4-tetrahydro-2-naphthalenecarboxylate obtained in Referential Example 5 was dissolved in 100 ml of anhydrous acetonitrile and then 3.22 g of sodium iodide and 3.94 g of 1-acetylimidazole were added thereto. The resulting mixture was heated under reflux for 1.5 hours. The reaction mixture was concentrated in vacuo and 100 ml of methanol was added to the residue. The mixture was stirred and concentrated in vacuo. Water was added to the residue. The mixture was neutralized by adding sodium bicarbonate and extracted with chloroform. The extract was washed with water, dried and then concentrated in vacuo. The residue was purified by silica gel column chromatography using a mixture of ethanol and chloroform (3:97 by volume) for elution to give an oily product. The product was suspended in ethanol, and an ethanolic solution of hydrogen chloride was added thereto. The mixure was concentrated to dryness in vacuo to give 4.8 g of ethyl 6-(1-imidazolylmethyl)-1,2,3,4-tetrahydro-2-naphthalenecarboxylate hydrochloride as colorless crystals with m.p. 170°-172° C.

1. temperatureThe resulting mixture was heated
2. temperatureunder reflux for 1.5 hours
3. concentrationThe reaction mixture was concentrated in vacuo and 100 ml of methanol
4. additionwas added to the residue
5. concentrationconcentrated in vacuo
6. additionWater was added to the residue
7. additionby adding sodium bicarbonate
8. extractionextracted with chloroform
9. washThe extract was washed with water
10. customdried
11. concentrationconcentrated in vacuo
12. customThe residue was purified by silica gel column chromatography
13. additiona mixture of ethanol and chloroform (3:97 by volume)
14. washfor elution
15. customto give an oily product
16. concentrationThe mixure was concentrated to dryness in vacuo

ORD record

ord-2ba32c270c5d40dd83bd48e74fe0b4d0

Source dataset

uspto-grants-1988_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04777257