Methyl 4-acetamido-5-chloro-2-(prop-2-yn-1-yloxy)benzoate synthesis
- Product Name:Methyl 4-acetamido-5-chloro-2-(prop-2-yn-1-yloxy)benzoate
- CAS Number:89481-87-8
- Molecular formula:C13H12ClNO4
- Molecular Weight:281.69
24190-77-0
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106-96-7
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89481-87-8
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Yield:89481-87-8 88.64%
Reaction Conditions:
with potassium carbonate in N,N-dimethyl-formamide at 0 - 20; for 28 h;
Steps:
1.iv Step (iv): Preparation of Methyl -acetyIamino-5-chloro-2-(propargyloxy) benzoate
Propargyl bromide (53.57 mL, 0.479 mole) was added to a stirred solution of methyl 4-acetylamino-5-chloro-2-hydroxy benzoate (97 grams, 0.399 mole, obtained in the above step) and potassium carbonate (K2CO3) (1 10.17 grams, 0.798 mole) in dimethylformamide (DMF) (1 L) at 0 °C. Then reaction mass was slowly allowed to rise to RT and stirred further for 28 hours at the same temperature, while monitoring the progress of the reaction by TLC. The mass was poured into chilled water (10 L) an'd stirred for 1 hour at RT. The resulting solid was filtered, washed with n-hexane (3 x 500 mL) and dissolved in EtOAc (3 L). The organic phase was washed with brine solution (500 mL), dried over Na2S04 and concentrated under vacuum to obtain the title compound. (0292) Weight: 99.6 grams (Yield: 88.64 %). (0293) - NMR (δ ppm): 2.15 (3H, s), 3.62 (1H, s), 3.77 (3H, s), 4.81 - 4.82 (2H, d), 7.75 (1 H, s), 7.90 (1H, s), 9.60 (1H, s); (0294) Mass (m/z): 282.0 (M+H)+, 284.1 (M+H)+.
References:
WO2016/128990,2016,A1 Location in patent:Page/Page column 27
4093-28-1
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$6.00/5g
89481-87-8
11 suppliers
$339.00/1g
65-49-6
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$6.00/25g
89481-87-8
11 suppliers
$339.00/1g
4136-97-4
180 suppliers
$6.00/5g
89481-87-8
11 suppliers
$339.00/1g