HCID 15337214, compound → HCID 15337215, compound

To a mixture of aqueous 20% TiCl3 (145 g, 0.188 mol), water (150 mL), and acetone (150 mL) was added dropwise a solution of 6-chloro-1-ethoxalyl-8-nitrotetralin (8.39 g, 0.027 mol) in acetone (150 mL) at 0° C. The mixture was stirred for 1 h at room temperature, diluted with water, and extracted with ethyl acetate (400 mL×2). The combined organic layers were washed successively with water and brine, dried over magnesium sulfate, and concentrated. The residue was dissolved in a mixture of THF (60 mL) and MeOH (60 mL) and 1N NaOH (60 mL) was added. The mixture was stirred for 2 h at room temperature, washed with diethyl ether (600 mL), acidified to pH 3 by using aqueous 5% KHSO4 and extracted with ethyl acetate (400 mL×2). The combined organic layers were washed successively with water and brine, dried over magnesium sulfate, and concentrated to give 2.07 g of the title compound: 1H NMR (CDCl3) δ8.57 (bs, 1H), 7.18 (s, 1H), 6.86 (s, 1H), 3.14 (t, 2H, J=6.1 Hz), 2.91 (t, 2H, J=6.1 Hz), 2.10 (m, 2H).

1. extractionextracted with ethyl acetate (400 mL×2)
2. washThe combined organic layers were washed successively with water and brine
3. dry with materialdried over magnesium sulfate
4. concentrationconcentrated
5. dissolutionThe residue was dissolved in a mixture of THF (60 mL) and MeOH (60 mL) and 1N NaOH (60 mL)
6. additionwas added
7. stirringThe mixture was stirred for 2 h at room temperature
8. washwashed with diethyl ether (600 mL)
9. extractionextracted with ethyl acetate (400 mL×2)
10. washThe combined organic layers were washed successively with water and brine
11. dry with materialdried over magnesium sulfate
12. concentrationconcentrated

ORD record

ord-91a475bf6fa442cebe2a1c9bc08d310a

Source dataset

uspto-grants-1996_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05496843