methyl 5-(acetylamino)-6-chloro-2H-chromene-8-carboxylate synthesis

6synthesis methods

Product Name:methyl 5-(acetylamino)-6-chloro-2H-chromene-8-carboxylate
CAS Number:132976-75-1
Molecular formula:C13H12ClNO4
Molecular Weight:281.69

89481-87-8 Synthesis

Methyl 4-acetamido-5-chloro-2-(prop-2-yn-1-yloxy)benzoate

89481-87-8
11 suppliers
$339.00/1g

methyl 5-(acetylamino)-6-chloro-2H-chromene-8-carboxylate

132976-75-1
9 suppliers
$152.00/1mg

Yield:132976-75-1 64.8%

Reaction Conditions:

with dowtherm A at 220; for 3 h;

Steps:

1.v Step (v)
Preparation of methyl 5-acetyIamino-6-chloro-2H-chromene-8- carboxylate

A stirred solution of methyl 4-acetylamino-5-chloro-2-(prop-2-ynyloxy) benzoate (25 grams, 88.8 mmol, obtained in above step) in dowtherm A (127 mL) was heated to 220 °C for 3 hours. The reaction mixture was cooled to 60-70 °C and dumped in hexane. The solids precipitated were filtered and washed with hexane to obtain methyl 5-acetylamino-6-chloro-2H-chromene-8-carboxylate (16.2 grams).Yield: 64.8 %.? - NMR (DMSO-d₆): δ 9.77 (s, 1H), 7.58 (s, 1H), 6.42 (d, J = 10.1 Hz, 1H), 6.04 (m, 1 H), 4.83 (s, 2H), 3.78 (s, 3H), 2.06 (s, 3H);Mass (m/z): 282, 284 (M+H)⁺.

References:

WO2013/42135,2013,A1 Location in patent:Page/Page column 12

4093-28-1 Synthesis