Ammonia → 1-(4-Bromonaphthalen-1-yl)methanamine hydrochloride

温度

-40 °C

A mixture of 1-bromo-4-methylnaphthaline (25 g, 0.113 mol), NBS (22.2 g, 0.123 mol) and benzoylperoxide (5 g) in CCl4 (750 mL) was refluxed for 5 h. The reaction mixture was cooled, filtered off the succinimide and concentrated to give crude bromide (34 g) and used for the next reaction without any purification. To a cold (−40° C.) solution of liquid ammonia (2 L) was added 1-bromo-4-bromomethyl naphthaline (crude 34 g) dissolved in 200 mL of CH2Cl2 over a period of 45 min. The reaction mixture was then stirred at −40° C. for 18 h. The reaction mixture was then allowed to stir at RT and concentrated under vacuum to give yellow residue. The residue was then treated with 3N HCl (250 mL), filtered off the solid obtained and washed with CH2Cl2 (2×250 mL). The solid was dried under vacuum to give (4-bromo-1-naphthyl)methylamine hydrochloride (25 g, 80%). HPLC purity: 96.6%

1. customused for the next reaction without any purification
2. stirringto stir at RT
3. concentrationconcentrated under vacuum
4. customto give yellow residue
5. filtrationfiltered off the solid
6. customobtained
7. washwashed with CH2Cl2 (2×250 mL)
8. customThe solid was dried under vacuum

ORDレコード

ord-876d34359d064bfd8395b9230214ebd6

出典データセット

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07592477B2