Pentane → (2-Aminophenyl)(3-methoxyphenyl)methanone

To a solution of bromoanisole 91 (1.38 mL, 10.7 mmol) in THF (5 mL) at 78° C. and under nitrogen atmosphere, was added 1.2 M t-BuLi in pentane (18.2 mL, 21.9 mmol) dropwise. After stirring for 20 min, anthranilonitrile 92 (0.63 g, 5.3 mmol) was added. The reaction was warmed to rt and stirred overnight. The reaction was cooled to 0° C. and quenched with 3N HCl. After stirring 30 min at rt, the acidic extracts were washed with EtOAc (3×12 mL). The aqueous layer was made basic (pH>10) using 6N NaOH and extracted with CH2Cl2. The organic extracts were washed with sat. NaCl, dried over NaSO4, filtered, and concentrated to give a crude mixture containing 93. The crude oil was purified by chromatography on silica to provide pure 93 (0.17 g, 14%) as a yellow oil; 1H NMR (500 MHz, DMSO-d6) δ 7.40–7.43 (m, 1H), 7.27–7.30 (m, 1H), 7.07–7.17 (m, 4H), 6.86–6.88 (m, 1H), 6.49–6.52 (m, 1H), 3.81 (s, 3H); CI MS m/z=228 [C14H13NO2+H]+.

1. stirringstirred overnight
2. temperatureThe reaction was cooled to 0° C.
3. customquenched with 3N HCl
4. stirringAfter stirring 30 min at rt
5. washthe acidic extracts were washed with EtOAc (3×12 mL)
6. extractionextracted with CH2Cl2
7. washThe organic extracts were washed with sat. NaCl
8. dry with materialdried over NaSO4
9. filtrationfiltered
10. concentrationconcentrated
11. customto give a crude mixture
12. additioncontaining 93
13. customThe crude oil was purified by chromatography on silica

ORD record

ord-5c14dd280f9a452e821bc266bfcbaaa4

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07053084B1