(2-aMino-5-Methoxyphenyl)phenylMethanone synthesis

7synthesis methods

Product Name:(2-aMino-5-Methoxyphenyl)phenylMethanone
CAS Number:17549-79-0
Molecular formula:C14H13NO2
Molecular Weight:227.26

104-94-9 Synthesis

104-94-9
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100-47-0
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$14.14/25gm:

(2-aMino-5-Methoxyphenyl)phenylMethanone

17549-79-0
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Yield:17549-79-0 27%

Reaction Conditions:

Stage #1: 4-methoxy-aniline;benzonitrilewith boron trichloride in toluene at 0; for 0.0833333 h;Inert atmosphere;
Stage #2: with aluminum (III) chloride at 20 - 115; for 8 h;

Steps:

7 Intermediate 7A: (2-Amino-5 -methoxyphenyl)(phenyl)methanone

[00190j To a stirred solution of BC13 (4.5 mL, 1M in DCM, 4.47 mmol) at 0 °C, was added a mixture of 4-methoxyaniline (0.5 g, 4.06 mmol) and benzonitrile (0.837 g, 8.12 mmol) in toluene (5 mL) slowly over a period of twenty five minutes under a nitrogen atmosphere. The mixture was stirred for five minutes at 0 °C and then A1C13 (0.595 g, 4.47 mmol) was added portion wise over a period of 2 minutes at 0 °C. The reactionmixture was allowed to warm to room temperature and then heated at 115 °C for eight hours. The reaction mixture was cooled to room temperature, and was sequentially quenched with ice cold water (1 mL) and 1 .5N aqueous HC1 (5 mL) over thirty minutes. The reaction mixture was further refluxed at 100 °C for two hours, cooled to 0 ° C and 10% aqueous NaHCO3 (20 mL) was added dropwise over fifteen minutes until the pHwas 8 .5. The aqueous layer was extracted with EtOAc (3 x 25 mL). The organic layers were combined and washed with brine (2 x 10 mL), dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by ISCO chromatography on silica gel using EtOAc/hexane (1:12) as eluent to afford Intermediate 7A. (0.25g, 27%). HPLC: RT=1.37 mm (MeOH/H20 with TFA, CHROMOLITH speed ROD C18 5 jim,4.6 x 30 mm, gradient = 3 mm, Flow = 5mL/min; Mobile Phase A: 10% MeOH-90% H20-0.1% TFA; Mobile Phase B: 90% MeOH-10% H20-0.1% TFA; wavelength = 220); MS(ES): m/z228 [M+H].

References:

WO2014/47393,2014,A1 Location in patent:Paragraph 00190