Dimethylformamide → 6-bromo-N-methyl-2-naphtamide

6-Bromo-2-naphthoic acid (10.1 g, 40.1 mmol) and N,N-dimethylformamide (4.75 g, 65.0 mmol) were added to toluene (80 mL). To the reaction mixture was added dropwise thionyl chloride (5.7 g, 48.2 mmol) at 45 to 50° C., and the mixture was stirred for 1 hr, and allowed to cool to room temperature. The reaction mixture was added dropwise at 10 to 25° C. to a solution prepared by adding triethylamine (11.4 g, 112.4 mmol) and 40% methylamine methanol solution (8.1 g, 104.4 mmol) to toluene (80 mL), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added dropwise water (50 mL), and the mixture was stirred at room temperature. The crystals were collected by filtration, and washed with a mixed solvent (25 mL) of methanol/water (2:8) to give wet crystals. The total amount of the wet crystals was added to N,N-dimethylacetamide (70 mL), and dissolved with heating to 60° C. The reaction mixture was allowed to cool to room temperature, and water (140 mL) was added dropwise thereto. The crystals were collected by filtration, and washed with water (80 mL) to give wet crystals. The total amount of the wet crystals was suspended in ethyl acetate (25 mL) with stirring at room temperature. The crystals were collected by filtration, and washed with ethyl acetate (5 mL). The obtained wet crystals were dried under reduced pressure to give 6-bromo-N-methyl-2-naphthamide (9.4 g, 35.6 mmol). yield 89%.

1. additionThe reaction mixture was added dropwise at 10 to 25° C. to a solution
2. customprepared
3. stirringthe mixture was stirred at room temperature for 1 hr
4. stirringthe mixture was stirred at room temperature
5. filtrationThe crystals were collected by filtration
6. washwashed with a mixed solvent (25 mL) of methanol/water (2:8)
7. customto give wet crystals
8. dissolutiondissolved
9. temperaturewith heating to 60° C
10. temperatureto cool to room temperature
11. filtrationThe crystals were collected by filtration
12. washwashed with water (80 mL)
13. customto give wet crystals
14. stirringwith stirring at room temperature
15. filtrationThe crystals were collected by filtration
16. washwashed with ethyl acetate (5 mL)
17. customThe obtained wet crystals were dried under reduced pressure

ORDレコード

ord-9bf6b4b530e34f16b80f13ea9660f441

出典データセット

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09278938B2