[2-Amino-5-(methyloxy)phenyl](4-chlorophenyl)methanone synthesis

5synthesis methods

Product Name:[2-Amino-5-(methyloxy)phenyl](4-chlorophenyl)methanone
CAS Number:91713-54-1
Molecular formula:C14H12ClNO2
Molecular Weight:261.7

4H-3,1-Benzoxazin-4-one, 6-Methoxy-2-Methyl-

38527-50-3
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[2-Amino-5-(methyloxy)phenyl](4-chlorophenyl)methanone

91713-54-1
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$165.00/500mg

Yield:91713-54-1 88%

Reaction Conditions:

Stage #1: 6-methoxy-2-methyl-4H-benzo[d][1,3]oxazin-4-one;4-chlorophenyl-magnesium bromide in diethyl ether;toluene at 0 - 20; for 1 h;
Stage #2: with hydrogenchloride;lithium hydroxide monohydrate in ethanol; for 2 h;Reflux;
Stage #3: with sodium hydroxide in ethyl acetate;

Steps:

79

Intermediate 79: [2-amino-5-(methyloxy)phenyll(4-chlorophenyl)methanone To a solution of Intermediate 83 (40.0 g, 0.21 mol, 1 equiv.) in a toluene/ether (2/1 ) mixture (760 mL) at 0°C was added dropwise a solution of 4-chlorophenylmagnesium bromide (170 mL, 1 M in Et₂0, 0.17 mol, 0.8 equiv.). The reaction mixture was allowed to warm to RT and stirred for 1 h before being quenched with 1 N HCI (200 mL). The aqueous layer was extracted with EtOAc (3 x 150 mL) and the combined organics were washed with brine (100 mL), dried over Na₂S0₄, filtered and concentrated under reduced pressure. The crude compound was then dissolved in EtOH (400 mL) and 6N HCI (160 mL) was added. The reaction mixture was refluxed for 2 h before being concentrated to one-third in volume. The resulting solid was filtered and washed twice with ether before being suspended in EtOAc and neutralised with 1 N NaOH. The aqueous layer was extracted with EtOAc (3 x 150 mL) and the combined organics were washed with brine (150 mL), dried over Na₂S0₄, filtered and concentrated under reduced pressure. The title compound was obtained as a yellow solid (39 g, 88 % yield); LC/MS: m/z 262 [M+H]+, Rt 2.57 min.

References:

WO2011/54844,2011,A1 Location in patent:Page/Page column 84