Methyl 4-amino-2-chlorobenzoate synthesis
- Product Name:Methyl 4-amino-2-chlorobenzoate
- CAS Number:46004-37-9
- Molecular formula:C8H8ClNO2
- Molecular Weight:185.61
67-56-1
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2457-76-3
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46004-37-9
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$6.00/250mg
Yield:46004-37-9 98%
Reaction Conditions:
with thionyl chloride at 0 - 20; for 32 h;
Steps:
125a Intermediate 125a: methyl 4-amino-2-chlorobenzoate
To a solution of 4-amino-2-chlorobenzoic acid (2 g, 1 1.66 mmol) in MeOH (55.5 mL) was added thionyl chloride (3.40 mL, 46.6 mmol) dropwise at 0°C. The resulting solution was stirred at rt. After 32h the solvent was removed. The crude product was taken up in EtOAc and washed with sat. aqueous NaHC03 and brine. The organic layer was dried over MgS04, filtered and evaporated to dryness to give intermediate 125a (2.146 g, 1 1.45 mmol, 98 % yield) as white solid.1 H NMR (400 MHz, DMSO-c/6) δ ppm 7.64 (d, J=8.56 Hz, 1 H), 6.64 (d, J=2.20 Hz, 1 H), 6.51 (dd, J=8.80, 2.20 Hz, 1 H), 6.16 (bs, 2 H), 3.73 (s, 3 H). Intermediate 125b: methyl 2-chloro-4-cvanobenzoate
References:
NOVARTIS AG;HEBACH, Christina;JOLY, Emilie;KALLEN, Joerg;TERNOIS, James Gilbert;TINTELNOT-BLOMLEY, Marina WO2013/8162, 2013, A1 Location in patent:Page/Page column 116
13324-11-3
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46004-37-9
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$6.00/250mg
2457-76-3
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77-78-1
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46004-37-9
160 suppliers
$6.00/250mg
2457-76-3
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75-36-5
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46004-37-9
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$6.00/250mg
99-60-5
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46004-37-9
160 suppliers
$6.00/250mg