Oxalyl chloride → HCID 21110101, compound

A solution of 6-methoxy-1,2,3,4-tetrahydroquinoline (10 g, 61.3 mmol) 600 mL CH2Cl2 was slowly added to a solution of oxalyl chloride (8.4 mL, 94.5 mmol) in 100 mL CH2Cl2 at 0° C. After addition the reaction mixture was at 0° C. for 0.5 h, aluminum chloride (24.5 g, 184 mmol) was than added to the reaction mixture, the resulting mixture was warmed up to room temperature, stirred over night. The reaction mixture was poured on ice, diluted with 1N HCl, the aqueous layer was extracted with CHCl3 (3×150 mL), the combined organic layers was washed with brine, dried over Na2SO4. The solvent was concentrated, the crude product was purified by flash chromatography (Hexane/EtOAc), obtained 10.0 g (75%) of pure title compound: 1H NMR (300 MHz, CDCl3) 2.01-2.05 (m, 2H), 2.74 (t, 2H, J=6.0 Hz), 3.73 (t, 2H, J=5.8 Hz), 3.77 (s, 3H), 6.92-6.93 (m, 2H).

1. additionAfter addition the reaction mixture
2. additionthan added to the reaction mixture
3. additionThe reaction mixture was poured on ice
4. extractionthe aqueous layer was extracted with CHCl3 (3×150 mL)
5. washthe combined organic layers was washed with brine
6. dry with materialdried over Na2SO4
7. concentrationThe solvent was concentrated
8. customthe crude product was purified by flash chromatography (Hexane/EtOAc)

ORD record

ord-024d2038a0d4478a8e059b382726bd6a

Source dataset

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07230011B2