3-Methoxybenzonitrile → 9-methoxy-2-(3-methoxyphenyl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one

温度

-30 °C

(Z)-2-(5-methoxy-3,4-dihydroisoquinolin-1(2H)-ylidene)-1-(3-methoxyphenyl)ethanimine. 1-1. A flask was charged with 5-methoxy-1-methyl-3,4-dihydroisoquinoline (3.0 g, 17.1 mmol) and Et2O (100 mL) under N2 and cooled to −30° C. A 2M solution of LDA (8.56 mL, 17.1 mmol) was added dropwise. The resulting brown suspension was stirred for 30 min at this temperature, and then cooled to −78° C. A solution of 3-methoxybenzonitrile (2.28 g, 17.1 mmol) in Et2O (25 mL) was added dropwise. The mixture was stirred at −78° C. for 1 h, and then allowed to warm to RT and stirred for another 18 h. the mixture was then poured onto H2O and extracted with AcOEt. The org. layers were dried over Na2SO4, filtered and concentrated in vacuo to give the title compound (5.9 g) as a brown oil that was used as it is in the next step. UPLC-MS: MS 309.3 (M+H+); UPLC rt 0.73 min.

1. temperaturecooled to −78° C
2. stirringThe mixture was stirred at −78° C. for 1 h
3. temperatureto warm to RT
4. stirringstirred for another 18 h. the mixture
5. additionwas then poured onto H2O
6. extractionextracted with AcOEt
7. dry with materiallayers were dried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORDレコード

ord-c16308862cae4d17a3a682c451458576

出典データセット

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08853203B2