6-(tert-Butyl)-3,4-dihydroisoquinolin-1(2H)-one → 6-tert-butyl-2H-isoquinolin-1-one

温度

100 °C

6-tert-Butyl-3,4-dihydro-2H-isoquinolin-1-one (1.709 g, 8.4 mmol) and 2,3-5,6-dicyano-p-benzoquinone (DDQ) (3.85 g, 2 eq) were taken up in dioxane (130 mL) and the resulting mixture was heated to 100° C. for four days. After allowing to cool to room temperature, most of the dioxane was removed under reduced pressure at 55° C. Ethyl acetate (300 mL) and 2N NaOH (100 mL) were added to the residue and the mixture was partitioned and the layers were sepearated. Subsequently washed again with 2N NaOH (3×100 mL), water (1×125 mL) and finally with brine (1×125 mL). The ethyl acetate layer was dried over magnesium sulfate, filtered and concentrated to give the crude product (1.783 G). Purification on silica gel eluting with 30% ethyl acetate in hexanes afforded the title compound (779 mg) as a light tan powder. MS (ESI) 202.0 (M+H)+.

1. customwas removed under reduced pressure at 55° C
2. additionEthyl acetate (300 mL) and 2N NaOH (100 mL) were added to the residue
3. customthe mixture was partitioned
4. washSubsequently washed again with 2N NaOH (3×100 mL), water (1×125 mL) and finally with brine (1×125 mL)
5. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customto give the crude product (1.783 G)
9. customPurification on silica gel eluting with 30% ethyl acetate in hexanes

ORDレコード

ord-bef0c51a110f4c0abab5af4ebb7259ff

出典データセット

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08299077B2